Pyrazolopyrimidines

ABSTRACT

Pyrazolopyrimidines of the formula 
                         
in which
 
R 1 , R 2 , R 3 , R 4 , R 5  and X are as defined in the description,
 
processes for preparing these compounds and their use for controlling unwanted microorganisms.

This application is a National Stage of International Application No.PCT/EP2006/001064, filed Feb. 7, 2006, which claims the benefit ofGerman Patent Application No. 10 2005 007534.7, filed Feb. 17, 2005. Theentirety of each of these applications is incorporated by referenceherein.

The invention relates to pyrazolopyrimidines, to a process for theirpreparation and to their use for controlling unwanted microorganisms.

It is already known that certain pyrazolopyrimidines have fungicidalproperties (see, for example, WO-A 02/048 151, WO-A 04/000 844, WO-A04/106 341 or WO-A 05/082 907).

However, since the ecological and economical demands made on modernfungicides are increasing constantly, for example with respect toactivity spectrum, toxicity, selectivity, application rate, formation ofresidues and favourable manufacture, and there can furthermore beproblems, for example, with resistance, there is a constant need todevelop novel fungicides which, at least in some areas, have advantagesover those of the prior art.

This invention now provides novel pyrazolopyrimidines of the formula (I)

in which the symbols are as defined below:

-   R¹ represents hydrogen, optionally substituted alkyl, optionally    substituted alkenyl, optionally substituted alkynyl, optionally    substituted cycloalkyl or optionally substituted heterocyclyl,    hydroxyl, optionally substituted alkoxy, amino, optionally    substituted alkylamino or optionally substituted dialkylamino;-   R² represents hydrogen or alkyl;-   or-   R¹ and R² together with the nitrogen atom to which they are attached    represent an optionally substituted heterocyclic ring;-   R³ represents optionally substituted aryl, optionally substituted    heterocyclyl, optionally substituted alkyl, optionally substituted    alkenyl, optionally substituted alkynyl, optionally substituted    cycloalkyl, optionally substituted cycloalkenyl, optionally    substituted aralkyl, halogen, an optionally substituted amino group,    optionally substituted (C₁-C₈)-alkoxy, optionally substituted    (C₁-C₈)-alkylthio, optionally substituted (C₆-C₁₀)-aryloxy,    optionally substituted (C₆-C₁₀)-arylthio, optionally substituted    heterocyclyloxy, optionally substituted    (C₆-C₁₀)-aryl-(C₁-C₄)-alkoxy, optionally substituted    (C₆-C₁₀)-aryl-(C₁-C₄)-alkylthio, optionally substituted    heterocyclyl-(C₁-C₄)-alkoxy, optionally substituted    heterocyclyl-(C₁-C₄)-alkylthio, C(S)OR⁸, C(O)SR⁸ or C(S)SR⁸;-   R⁴ represents CONR⁶R⁷;-   R⁵ represents H, halogen, optionally halogen-substituted alkyl or    optionally halogen-substituted cycloalkyl, O—(C₁-C₄)-alkyl or    S(O)₀₋₂(C₁-C₄)-alkyl;-   X represents halogen, cyano, hydroxyl, optionally substituted alkyl,    (C₁-C₃)-haloalkyl, optionally substituted alkoxy, optionally    substituted phenyl, optionally substituted alkylthio, optionally    substituted alkylsulphinyl or optionally substituted alkylsulphonyl;-   R⁶ represents H, a cation, for example an optionally alkyl- or    arylalkyl-substituted ammonium ion, optionally substituted alkyl,    optionally substituted alkenyl, optionally substituted alkynyl,    optionally substituted cycloalkyl and optionally substituted    cycloalkenyl, optionally substituted aryl and optionally substituted    arylalkyl;-   R⁷ represents COR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂, where the    radicals R⁸ may be identical or different, saturated, partially or    fully unsaturated or aromatic, optionally substituted 5- or    6-membered heterocyclyl which optionally contains 1 or up to three    further heteroatoms selected from N, S and/or O atoms, where oxygen    atoms may not be adjacent to one another;-   R⁸ independently of the other radicals represents H, optionally    substituted alkyl, haloalkyl, optionally substituted alkenyl,    optionally substituted alkynyl, optionally substituted cycloalkyl,    optionally substituted cycloalkenyl, optionally substituted aryl or    optionally substituted aralkyl; or two radicals R⁸ form a cycle    having 3 to 6 carbon atoms which is saturated or partially    unsaturated and, if appropriate, contains 1 or 2 further N, S or O    atoms, where oxygen atoms may not be adjacent to one another;-   or-   R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they    are attached form a 4- to 8-membered cycle which may contain one or    more heteroatoms from the group consisting of sulphur, oxygen and    nitrogen, where oxygen atoms may not be adjacent to one another;    and agrochemically active salts thereof.

Pyrazolopyrimidines of the formula (I) are highly suitable forcontrolling unwanted microorganisms. Especially, they have strongfungicidal activity and can be used both in crop protection and in theprotection of materials.

The compounds of the formula (I) can be present both in pure form and asmixtures of different possible isomeric forms, in particular ofstereoisomers, such as E and Z, threo and erythro and also opticalisomers, such as R and S isomers or atropisomers, and, if appropriate,also of tautomers. The invention encompasses both the pure isomers andtheir mixtures.

Depending on the nature of the substituents defined above, the compoundsof the formula (I) have acidic or basic properties and are capable offorming salts, if appropriate also inner salts. If the compounds of theformula (I) carry hydroxyl groups, carboxyl groups or other groups whichinduce acidic properties, these compounds can be reacted with bases toform salts. Suitable bases are, for example, hydroxides, carbonates,bicarbonates of the alkali metals and alkaline earth metals, inparticular those of sodium, potassium, magnesium and calcium,furthermore ammonia, primary, secondary and tertiary amines having(C₁-C₄)-alkyl radicals, mono-, di- and trialkanolamines of(C₁-C₄)-alkanols, choline and chlorocholine. If the compounds of theformula (I) carry amino groups, alkylamino groups or other groups whichinduce basic properties, these compounds can be reacted with acids togive salts. Suitable acids are, for example, mineral acids, such ashydrochloric acid, sulphuric acid and phosphoric acid, organic acids,such as acetic acid or oxalic acid, and acidic salts, such as NaHSO₄ andKHSO₄. The salts obtainable in this manner also have fungicidalproperties.

The formula (I) provides a general definition of the pyrazolopyrimidinesaccording to the invention.

Preference is given to compounds of the formula (I) in which R⁶ has oneof the following meanings:

a¹: H,

a²: cation,

a³: optionally substituted alkyl,

a⁴: optionally substituted alkenyl,

a⁵: optionally substituted alkynyl,

a⁶: optionally substituted cycloalkyl,

a⁷: optionally substituted cycloalkenyl,

a⁸: optionally substituted aryl or

a⁹: optionally substituted arylalkyl.

Preference is also given to compounds of the formula (I) in which R⁷ hasone of the following meanings:

a¹′: COR⁸,

a²′: SO₁₋₂R⁸,

a³′: cyano,

a⁴′: COOR⁸,

a⁵′: CON(R⁸)₂, where the radicals R⁸ can be identical or different, or

a⁶′: saturated, partially unsaturated or aromatic, optionallysubstituted 5- or 6-membered heterocyclyl.

Preference is also given to compounds of the formula (I) in which R⁶═Hor a cation and R⁷ has one of the following meanings:

a¹′: COR⁸,

a²′: SO₁₋₂R⁸,

a³′: cyano,

a⁴′: COOR⁸,

a⁵′: CON(R⁸)₂, where the radicals R⁸ can be identical or different, or

a⁶′: saturated, partially unsaturated or aromatic, optionallysubstituted 5- or 6-membered heterocyclyl.

Preference is also given to compounds of the formula (I) in which R⁶ hasone of the following meanings:

a^(1″): a¹, a², a³, a⁴, a⁵, a⁶, a⁷, a⁸,

a^(2″): a¹, a², a³, a⁴, a⁵, a⁶, a⁷, a⁹,

a^(3″): a¹, a², a³, a⁴, a⁵, a⁶, a⁸, a⁹,

a^(4″): a¹, a², a³, a⁴, a⁵, a⁷, a⁸, a⁹,

a^(5″): a¹, a², a³, a⁴, a⁶, a⁷, a⁸, a⁹,

a^(6″): a¹, a², a³, a⁵, a⁶, a⁷, a⁸, a⁹,

a^(7″): a¹, a², a⁴, a⁵, a⁶, a⁷, a⁸, a⁹,

a^(8″): a¹, a³, a⁴, a⁵, a⁶, a⁷, a⁸, a⁹,

a^(9″): a², a³, a⁴, a⁵, a⁶, a⁷, a⁸, a⁹.

Preference is also given to compounds of the formula (I) in which R⁷ hasone of the following meanings:

a^(1′″): a^(1′), a^(2′), a^(3′), a^(4′), a^(5′),

a^(2′″): a^(1′), a^(2′), a^(3′), a^(4′), a^(6′),

a^(3′″): a^(1′), a^(2′), a^(3′), a^(5′), a^(6′),

a^(4′″): a^(1′), a^(2′), a^(4′), a^(5′), a^(6′),

a^(5′″): a^(1′), a^(3′), a^(4′), a^(5′), a^(6′),

a^(6′″): a^(2′), a^(3′), a^(4′), a^(5′), a^(6′).

Preference is furthermore given to compounds of the formula (I) in which

b¹) R³ represents optionally substituted aryl, or

b²) R³ represents optionally substituted heterocyclyl, or

b³) R³ represents optionally substituted alkyl, or

b⁴) R³ represents optionally substituted alkenyl, or

b⁵) R³ represents optionally substituted alkynyl, or

b⁶) R³ represents optionally substituted cycloalkyl, or

b⁷) R³ represents optionally substituted aralkyl, or

b⁸) R³ represents an optionally substituted amino group, or

b⁹) R³ represents optionally substituted (C₁-C₈)-alkylthio, or

b¹⁰) R³ represents optionally substituted (C₁-C₈)-alkoxy.

Preference is also given to compounds of the formula (I) in which R³ hasone of the following meanings:

c¹: b¹, b², b³, b⁴, b⁵, b⁶, b⁷, b⁸, b⁹

c²: b¹, b², b³, b⁴, b⁵, b⁶, b⁷, b⁸, b¹⁰

c³: b¹, b², b³, b⁴, b⁵, b⁶, b⁷, b⁹, b¹⁰

c⁴: b¹, b², b³, b⁴, b⁵, b⁶, b⁸, b⁹, b¹⁰

c⁵: b¹, b², b³, b⁴, b⁵, b⁷, b⁸, b⁹, b¹⁰

c⁶: b¹, b², b³, b⁴, b⁶, b⁷, b⁸, b⁹, b¹⁰

c⁷: b¹, b², b³, b⁵, b⁶, b⁷, b⁸, b⁹, b¹⁰

c⁸: b¹, b², b⁴, b⁵, b⁶, b⁷, b⁸, b⁹, b¹⁰

c⁹: b¹, b³, b⁴, b⁵, b⁶, b⁷, b⁸, b⁹, b¹⁰

c¹⁰: b², b³, b⁴, b⁵, b⁶, b⁷, b⁸, b⁹, b¹⁰

Preference is furthermore given to those compounds of the formula (I) inwhich one or more symbols have one of the preferred meanings givenbelow, i.e.

-   R¹ represents hydrogen, alkyl having 1 to 10 carbon atoms which is    unsubstituted or mono- to pentasubstituted by identical or different    substituents from the group consisting of halogen, cyano, hydroxyl,    alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon    atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono-    or dialkylamino having in each case 1 to 4 carbon atoms, or-   R¹ represents alkenyl having 2 to 10 carbon atoms which is    unsubstituted or mono- to trisubstituted by identical or different    substituents from the group consisting of halogen, cyano, hydroxyl,    alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon    atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono-    or dialkylamino having in each case 1 to 4 carbon atoms, or-   R¹ represents alkynyl having 2 to 10 carbon atoms which is    unsubstituted or mono- to trisubstituted by identical or different    substituents from the group consisting of halogen, cyano, hydroxyl,    alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon    atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono-    or dialkylamino having in each case 1 to 4 carbon atoms, or-   R¹ represents cycloalkyl having 3 to 10 carbon atoms which is    unsubstituted or mono- to trisubstituted by identical or different    substituents from the group consisting of halogen and alkyl having 1    to 4 carbon atoms, or-   R¹ represents saturated or unsaturated heterocyclyl having 3 to 10    ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and/or    sulphur, where the heterocyclyl is unsubstituted or mono- or    polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano,    nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxyl, alkoxy    having 1 to 4 carbon atoms and/or mercapto;-   R² represents hydrogen or alkyl having 1 to 6 carbon atoms;-   R¹ and R² together with the nitrogen atom to which they are attached    represent a saturated or unsaturated heterocyclic ring having 3 to 8    ring members, where the heterocycle optionally contains a further    nitrogen, oxygen or sulphur atom as ring member and where the    heterocycle may be unsubstituted or up to trisubstituted by    fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms,    haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine and/or    chlorine atoms, hydroxyl, alkoxy having 1 to 4 carbon atoms,    haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine and/or    chlorine atoms, mercapto, thioalkyl having 1 to 4 carbon atoms    and/or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine    and/or chlorine atoms;-   R³ represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    C₃-C₈-cycloalkyl, phenyl-C₁-C₁-alkyl, where R³ is unsubstituted or    partially or fully halogenated and/or optionally carries one to    three radicals from the group R^(x), or C₁-C₁₀-haloalkyl which    optionally carries one to three radicals from the group R^(x), and    R^(x) represents cyano, nitro, hydroxyl, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl,    C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,    C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,    C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy and    optionally halogenated oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy,    oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy, oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy, or-   R³ represents phenyl which may be mono- to tetrasubstituted by    identical or different substituents from the group consisting of    -   halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl,        carboxyalkyl, carbamoyl, thiocarbamoyl;    -   in each case straight-chain or branched alkyl, alkoxy,        alkylthio, alkylsulphinyl or alkylsulphonyl having in each case        1 to 6 carbon atoms;    -   in each case straight-chain or branched alkenyl or alkenyloxy        having in each case 2 to 6 carbon atoms;    -   in each case straight-chain or branched haloalkyl, haloalkoxy,        haloalkylthio, haloalkylsulphinyl or haloalkylsulphonyl having        in each case 1 to 6 carbon atoms and 1 to 13 identical or        different halogen atoms;    -   in each case straight-chain or branched haloalkenyl or        haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to        11 identical or different halogen atoms;    -   in each case straight-chain or branched alkylamino,        dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl,        alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in        each case 1 to 6 carbon atoms in the individual alkyl moieties;    -   cycloalkyl having 3 to 8 carbon atoms;    -   2,3-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy        (—O—CH₂—O—) or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—), where these        radicals may be mono- or polysubstituted by identical or        different substituents from the group consisting of halogen,        alkyl having 1 to 4 carbon atoms and haloalkyl having 1 to 4        carbon atoms and 1 to 9 identical or different halogen atoms;-   or-   R³ represents saturated or fully or partially unsaturated or    aromatic heterocyclyl having 3 to 8 ring members and 1 to 3    heteroatoms from the group consisting of nitrogen, oxygen and    sulphur, where the heterocyclyl may be mono- or disubstituted by    halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4    carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkoxy    having 1 to 4 carbon atoms, haloalkylthio having 1 to 4 carbon    atoms, hydroxyl, mercapto, cyano, nitro and/or cycloalkyl having 3    to 6 carbon atoms and/or carboxyalkyl;-   or-   R³ represents C₁-C₈-alkylamino, C₂-C₈-alkenylamino,    C₂-C₈-alkynylamino, di-C₁-C₈-alkylamino, di-C₂-C₈-alkenylamino,    di-C₂-C₈-alkynylamino, C₂-C₈-alkenyl-(C₂-C₈)-alkynylamino,    C₂-C₆-alkynyl-(C₁-C₈)-alkylamino, C₂-C₈-alkenyl-(C₁-C₈)-alkylamino,    C₆-C₁₀-arylamino, C₆-C₁₀-aryl-(C₁-C₈)-alkylamino,    C₆-C₁₀-aryl-(C₁-C₄)-alkyl-(C₁-C₈)-alkylamino,    heterocyclyl-(C₁-C₈)-alkylamino or    heterocyclyl-(C₁-C₄)-alkyl-(C₁-C₈)-alkylamino;-   R⁴ represents CONR⁶R⁷;-   R⁵ represents H, halogen, (C₁-C₄)-alkyl which is unsubstituted or    substituted by one or more halogen atoms, cyclopropyl which is    unsubstituted or substituted by one or more halogen atoms; SCH₃,    SOCH₃, SO₂CH₃ or OCH₃;-   X represents H, fluorine, chlorine, bromine, CN, hydroxyl, alkoxy    having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms or    (C₁-C₇)-alkyl or (C₁-C₃)-haloalkyl;-   R⁶ represents H, an alkali metal or alkaline earth metal, copper,    NH₄, mono-(C₁-C₁₀)-alkylammonium, di-(C₁-C₁₀)-alkylammonium,    tri-(C₁-C₁₀)-alkylammonium, tetra-(C₁-C₁₀)-alkylammonium, where the    alkyl radicals of the ammonium ions may be substituted by aryl or    hydroxyl, cholinium, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, aryl, phenyl-C₁-C₁₀-alkyl,    where R⁶ is unsubstituted or partially or fully halogenated and/or    optionally carries one to three radicals from the group Rx, or    C₁-C₁₀-haloalkyl which optionally carries one to three radicals from    the group R^(x), and R^(x) represents cyano, nitro, hydroxyl,    C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino,    di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl,    C₃-C₆-alkynyloxy and optionally halogenated    oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy, oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy,    oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy and/or CONR⁶R⁷, CONR⁷OR⁷, COOR⁸,    carboxy-(C₁-C₄)-alkyl;-   R⁷ represents COR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂, where the    radicals R⁸ may be identical or different, or

-   A, B, D, E, G are identical or different and are CR⁹, CR⁹R⁹, N, NR⁹,    O or S, with the proviso that at least one symbol represents N, O or    S and that the oxygen atoms are not adjacent to one another;-   Y represents C, CR⁹ or N;-   R⁸ independently of the other radicals represents H, C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkenyl, aryl, phenyl-C₁-C₁₀-alkyl, where R⁸ is    unsubstituted or partially or fully halogenated and/or optionally    carries one to three radicals from the group R^(x), or    C₁-C₁₀-haloalkyl which optionally carries one to three radicals from    the group R^(x), and Rx represents cyano, nitro, hydroxyl,    C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino,    di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl,    C₃-C₆-alkynyloxy and optionally halogenated    oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy, oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy,    oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy; or two radicals R⁸ form a cycle    having 3 to 6 carbon atoms which is saturated or partially    unsaturated and optionally contains 1 or 2 further N, S or O atoms,    where the oxygen atoms may not be adjacent to one another;-   or-   R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they    are attached form a 4- to 8-membered cycle which may contain one or    more heteroatoms from the group consisting of sulphur, oxygen and    nitrogen, where oxygen atoms may not be adjacent to one another;-   R⁹ represents R⁷, H, halogen, NR⁷ ₂, OH, SR⁷ or OR⁷.

Particular preference is given to those pyrazolopyrimidines of theformula (I) in which one or more of the symbols have one of theparticularly preferred meanings listed below, i.e.

-   R¹ represents hydrogen or a radical of the formula

where # denotes the point of attachment (here, these radicals may bepresent both in optically pure form and in isomer mixtures);

-   R² represents hydrogen, methyl, ethyl, propyl, or-   R¹ and R² together with the nitrogen atom to which they are attached    represent pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl,    piperazinyl, 3,6-dihydro-1(2H)-pyridinyl or    tetrahydro-1(2H)-pyridazinyl, where these radicals are unsubstituted    or substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and/or    trifluoromethyl,-   or-   R¹ and R² together with the nitrogen atom to which they are attached    represent a radical of the formula

-   -   in which    -   R′ represents hydrogen or methyl,    -   R″ represents methyl, ethyl, fluorine, chlorine or        trifluoromethyl,

-   m represents the number 0, 1, 2 or 3, where R″ represents identical    or different radicals if m represents 2 or 3,

-   R′″ represents methyl, ethyl, fluorine, chlorine or trifluoromethyl

-   and

-   n represents the number 0, 1, 2 or 3, where R′″ represents identical    or different radicals if n represents 2 or 3,

-   R³ represents (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    (C₃-C₈)-cycloalkyl, where R³ is unsubstituted or substituted by one    or more fluorine or chlorine atoms, benzyl or

-   R³ represents phenyl which may be mono- to trisubstituted by    identical or different substituents from the group consisting of    -   fluorine, chlorine, bromine, cyano, nitro, formyl, methyl,        ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, ethynyl,        allyl, propargyl, methoxy, ethoxy, n- or i-propoxy, methylthio,        ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,        methylsulphonyl, ethylsulphonyl, allyloxy, propargyloxy,        trifluoromethyl, trifluoroethyl, difluoromethoxy,        trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,        difluoromethylthio, difluorochloromethylthio,        trifluoromethylthio, trifluoromethylsulphinyl,        trifluoromethylsulphonyl, trichloroethynyloxy,        trifluoroethynyloxy, chloroallyloxy, iodopropargyloxy,        methylamino, ethylamino, n- or i-propylamino, dimethylamino,        diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl,        ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl,        methoximinomethyl, ethoximinomethyl, methoximinoethyl,        ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or        cyclohexyl, or by    -   2,3-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy        (—O—CH₂—O—) or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—), where these        radicals may be mono- or polysubstituted by identical or        different substituents from the group consisting of fluorine,        chlorine, methyl, ethyl, n-propyl, i-propyl, trifluoromethyl,        carboxyl and carboxymethyl,

-   R³ represents pyridyl which is attached in the 2- or 4-position and    may be mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, cyano, hydroxyl, mercapto, nitro, methyl, ethyl, methoxy,    methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or

-   R³ represents pyrimidyl which is attached in the 2- or 4-position    and may be mono- to trisubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,    methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or

-   R³ represents thienyl which is attached in the 2- or 3-position and    may be mono- to trisubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,    methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or

-   R³ represents C₁-C₈-alkylamino or di-C₁-C₈-alkylamino, or

-   R³ represents thiazolyl which is attached in the 2-, 4- or    5-position and may be mono- or disubstituted by identical or    different substituents from the group consisting of fluorine,    chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl,    methoxy, methylthio, hydroximinomethyl, hydroximinoethyl,    methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxyl and    carboxymethyl or

-   R³ represents N-piperidinyl, N-tetrazolyl, N-pyrazolyl,    N-imidazolyl, N-1,2,4-triazolyl, N-pyrrolyl or N-morpholinyl which    are in each case unsubstituted or mono- or—if    possible—polysubstituted by identical or different substituents from    the group consisting of fluorine, chlorine, bromine, cyano, nitro,    hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,    hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl and trifluoromethyl,

-   R⁴ represents CONR⁶R⁷;

-   R⁵ represents H, Cl, F, CH₃, —CH(CH₃)₂ or cyclopropyl; a X    represents H, F, Cl, CN, C₁-C₄-alkyl which is unsubstituted or    substituted by one or more fluorine or chlorine atoms; and

-   R⁶ represents H, Na, K, ½Ca, ½Mg, Cu, NH₄, NH(CH₃)₃, N(CH₃)₄,    HN(C₂H₅)₃, N(C₂H₅)₄, H₂N(iC₃H₇)₂, H₃NCH₂Ph, (H₃C)₃NCH₂Ph, cholinium,    (C₁-C₈)-alkyl, (C₃-C₆)-alkenyl, (C₁-C₈)-cycloalkenyl,    (C₁-C₈)-cycloalkyl, phenyl, benzyl;

-   R⁷ represents COR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂, where the    radicals R⁸ may be identical or different, pyrrolyl, imidazolyl,    pyrazolyl, 1,3,4-triazolyl, thiazolyl, isothiazolyl,    1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, oxazolyl, isoxazolyl,    tetrazolyl, oxadiazinyl, 4H-[1,2,4]-oxadiazin-3-yl, dioxazinyl,    5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, pyrimidinyl, pyrazinyl,    pyridazinyl, where the heterocyclic radicals are optionally    substituted by one or more radicals from the group consisting of    C₁-C₄-alkyl, C₁-C₄-alkoxy and halogen;

-   R⁸ independently of the other radicals represents H, (C₁-C₈)-alkyl,    (C₁-C₈)-haloalkyl, (C₂-C₆)-alkenyl, propargyl, (C₃-C₈)-cycloalkyl,    benzyl; or two radicals R⁸ form a cycle having 3 to 6 carbon atoms    which is saturated or partially unsaturated and optionally contains    1 or 2 further N, S or O atoms, where oxygen atoms may not be    adjacent to one another;

-   or

-   R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they    are attached form a 4- to 8-membered cycle which may contain one or    more heteroatoms from the group consisting of sulphur, oxygen and    nitrogen, where oxygen atoms may not be adjacent to one another.

Very particular preference is given to compounds of the formula (I) inwhich one or more of the symbols have one of the very particularlypreferred meanings listed below, i.e.

-   R¹ and R² have the particularly preferred meanings listed above;-   R³ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    (C₃-C₈)-cycloalkyl, where R³ is unsubstituted or substituted by one    or more fluorine or chlorine atoms and/or alkyl,-   or-   R³ represents 2,4-, 2,5- or 2,6-disubstituted phenyl, or    2-substituted phenyl or represents 2,4,6- or 2,4,5-trisubstituted    phenyl having substituents from the group consisting of fluorine,    chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl,    methoxy, methylthio, hydroximinomethyl, hydroximinoethyl,    methoximinomethyl, methoximinoethyl, carboxyl and carboxymethyl or-   R³ represents pyridyl which is attached in the 2- or 4-position and    may be mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, cyano, hydroxyl, mercapto, methyl, ethyl, methoxy,    methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, and carboxymethyl or-   R³ represents pyrimidyl which is attached in the 4-position and may    be mono- to trisubstituted by identical or different substituents    from the group consisting of fluorine, chlorine, bromine, cyano,    hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,    hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, and carboxymethyl or-   R³ represents thienyl which is attached in the 2- or 3-position and    may be mono- to trisubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,    methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or-   R⁴ represents CONR⁶R⁷;-   R⁵ represents H, —CH₃, —CH(CH₃)₂, Cl or cyclopropyl; and-   X represents fluorine, chlorine, (C₁-C₇)-alkyl or (C₁-C₃)-haloalkyl;-   R⁶ represents H, Na, K, NH₄, HN(Et)₂, H₂N(iPr)₂, H₃NCH₂Ph,    (H₃C)₃NCH₂Ph, benzyl, (C₃-C₈)-cycloalkyl, propargyl,    (C₃-C₆)-alkenyl, (C₁-C₈)-alkyl, fully or partially substituted by F    and/or Cl and/or carboxy-(C₁-C₄)-alkyl, CONR⁶R⁷, CONR⁷OR⁷, COOR⁸;-   R⁷ represents COR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂, where the    radicals R⁸ may be identical or different, 1H-pyrrolyl,    1H-imidazolyl, 1H-pyrazolyl, isoxazolyl, oxazolyl,    1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl,    1H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl,    4H-[1,2,4]-oxadiazin-3-yl, dioxazinyl,    5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, where the heterocyclic    radicals are optionally substituted by one or more radicals from the    group consisting of C₁-C₄-alkyl and halogen;-   R⁸ independently of the other radicals represents H, methyl, ethyl,    propyl, i-propyl, butyl, i-butyl, sec-butyl, t-butyl, pentyl, hexyl,    (C₁-C₃)-haloalkyl, (C₂-C₆)-alkenyl, propargyl, (C₃-C₆)-cycloalkyl,    benzyl;-   or-   R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they    are attached form a 4- to 8-membered cycle which may contain one or    more heteroatoms from the group consisting of sulphur, oxygen and    nitrogen, where oxygen atoms may not be adjacent to one another.

Very particular preference is furthermore given to compounds of theformula (I) in which one or more of the symbols have one of the veryparticularly preferred meanings listed below, i.e.

-   R¹ and R² have the particularly preferred meanings given above;-   R³ represents 2,4-, 2,5- or 2,6-disubstituted phenyl, or    2-substituted phenyl or represents 2,4,6- or 2,4,5-trisubstituted    phenyl having substituents from the group consisting of fluorine,    chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl,    methoxy, methylthio, hydroximinomethyl, hydroximinoethyl,    methoximinomethyl, methoximinoethyl, carboxyl and carboxymethyl or-   R³ represents thienyl which is attached in the 2- or 3-position and    may be mono- to trisubstituted by identical or different    substituents from the group consisting of fluorine, chlorine,    bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,    methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,    methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or-   R⁴ represents CONR⁶R⁷;-   X represents fluorine, chlorine, methyl or trifluoromethyl;-   R⁵ represents H, —CH₃;-   R⁶ represents H, Na, K, NH₄, HN(Et)₂, H₂N(iPr)₂, H₃NCH₂Ph,    (H₃C)₃NCH₂Ph, benzyl, (C₃-C₈)-cycloalkyl, propargyl,    (C₃-C₆)-alkenyl, (C₁-C₈)-alkyl, fully or partially substituted by F    and/or Cl and/or carboxy-(C₁-C₄)-alkyl, CONR⁶R⁷, CONR⁷OR⁷, COOR⁸;-   R⁷ represents COR⁸, S(O)R⁸, COOR⁸, 1H-pyrrolyl, 1H-imidazolyl,    1H-pyrazolyl, isoxazolyl, oxazolyl, 1,3,4-oxadiazolyl,    1,3,4-thiadiazolyl, thiazolyl, isothiazolyl, 1H-1,3,4-triazolyl,    tetrazolyl, oxadiazinyl, 4H-[1,2,4]-oxadiazin-3-yl, dioxazinyl,    5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, where the heterocyclic    radicals are optionally substituted by one or more radicals from the    group consisting of C₁-C₄-alkyl and halogen;-   R⁸ independently of the other radicals represents H, methyl, ethyl,    propyl, i-propyl, butyl, i-butyl, sec-butyl, t-butyl, pentyl, hexyl,    (C₁-C₃)-haloalkyl, (C₂-C₆)-alkenyl, propargyl, (C₃-C₆)-cycloalkyl,    benzyl;-   or-   R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they    are attached form a 4- to 8-membered cycle which may contain one or    more heteroatoms from the group consisting of sulphur, oxygen and    nitrogen, where oxygen atoms may not be adjacent to one another.

The radical definitions mentioned above may be combined with one anotheras desired. Moreover, individual definitions may not apply.

Compounds of the formula (I) in which R⁴ represents CONR⁶R⁷ and Xrepresents Cl (formula Ia in Scheme 1) can be prepared, for example, asshown in Scheme 1 starting with 3-aminopyrazole-4-carboxylic esters (II)which are known from the literature (see, for example, U.S. Pat. No.3,515,715 and U.S. Pat. No. 3,634,391) and malonic esters (IIa) whereR¹¹=C₁-C₈-alkyl or aryl:

The malonic esters (IIa) are known from the literature or can beprepared by processes known from the literature (for example WO04/006913, WO 04/005876, (R³=heterocyclyl), U.S. Pat. No. 6,156,925(R³=substituted phenyl), WO-A 03/009687 (R³=substituted alkyl), Chem.Ber. 1956, 89, 996 (R³=substituted cycloalkyl)).

Malonic esters of the formula (IIa) where R³=(2-chloro- or-methyl)thiophen-3-yl (compounds of the formula II b in Scheme 1a) canalso be prepared according to Scheme 1a below:

Analogously to the last two steps of the synthesis sequence, dimethyl2-(2-chlorothiophen-3-yl)malonate can also be prepared from(2-chlorothiophen-3-yl)acetic acid.

The step-wise conversion of the starting materials (II) into the amine(V) can be carried out, for example, analogously to the processes givenin WO 04/000 844 and in WO 05/082 907. The intermediates II, IV, V, VIand VII and their conversion into one another according to Scheme 1 arealready known from WO 05/082 907.

The compounds VIII (amines, amides, sulphonamides, carbamates, ureas andamino-substituted heterocycles) used for further conversion of the acidchlorides (VII) are known. They are commercially available or can beprepared by known processes which are familiar to the person skilled inthe art, as described, for example, in Houben-Weyl, Methoden derOrganischen Chemie [Methods of Organic Chemistry] or else Adv.Heterocycl. Chem. 1998, 72, 79-116 (and the literature cited therein).

Novel and thus also part of the subject-matter of the present inventionis the reaction of the acid chlorides VII with the compounds of theformula VIII to give compounds of the formula Ia.

Alternatively to the process given in Scheme 1, compounds of the formulaI in which R⁴ represents CONR⁶R⁷, R⁷ represents COR⁸, S(O)₁₋₂R⁸ and Hetand X represents Cl (compounds of the formula Ia in Scheme 2) can besynthesized by reacting the amides of the formula IX with halogencompounds of the formula X, for example. The amides of the formula XIobtained in this manner are then reacted either with halogen compoundsXII or with compounds XIII to give the end products Ia.

The amides of the formula IX in which R³ represents optionallysubstituted phenyl and a process for their preparation are known from WO05/0056556. Amides of the formula IX in which R³ represents optionallysubstituted heterocyclyl can be prepared by reacting the3-cyanopyrazolopyrimidines known from WO 05/000851 analogously to theprocess given in WO 05/0056556 to give the corresponding amides of theformula IX. Amides of the formula IX in which R³ represents optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted cycloalkyl or optionally substituted cycloalkenyl can beprepared by reacting the 3-cyanopyrazolopyrimidines known from WO05/056557 analogously to the process given in WO 05/0056556 to give thecorresponding amides of the formula IX. The halogen compounds of theformula X (for example acid chlorides, chloroformic half-esters,sulphonyl chlorides, heterocyclically substituted carbonyl chlorides)required for the further reactions are known. They are commerciallyavailable or can be prepared by processes which are familiar to theperson skilled in the art, as described, for example, in HOUBEN WEYL,Methoden der Organischen Chemie. The halogen compounds of the formulaXII (for example alkyl halides, alkenyl halides, alkynyl halides,cycloalkyl halides, cycloalkenyl halides, aryl halides, aralkyl halides)required for the further reactions are likewise known. They arecommercially available or can be prepared by processes which arefamiliar to the person skilled in the art, as described, for example, inHOUBEN WEYL, Methoden der Organischen Chemie. The compounds of theformula XIII (for example metal hydrides, metal hydroxides, amines,where metal represents, for example, alkali metals, alkaline earthmetals) required for the further reactions are likewise known. They arecommercially available or can be prepared by processes familiar to theperson skilled in the art, as described, for example, in HOUBEN WEYL,Methoden der Organischen Chemie.

Novel and thus likewise part of the subject-matter of the presentinvention is the step-wise conversion of the amides IX with the halogencompounds of the formula X into compounds of the formula XI and thefurther reaction either with halogen compounds of the formula XII orcompounds of the formula XIII to compounds of the formula Ia.

Compounds of the formula (I) in which X represents a cyano group(compounds of the formula Ib in Scheme 3) can be prepared, for example,as shown in Scheme 3 starting with the intermediates (V).

The reaction of compounds of the formula V with cyanide to givecompounds of the formula Va is carried out under standard conditionsknown from the literature (for example: J. Heterocycl. Chem. 1993,30(4), 993-5). Novel and thus likewise part of the subject-matter of thepresent invention is the reaction of the acid chlorides VIIa withcompounds of the formula VIII to give compounds of the formula Ib.

Compounds of the formula (I) in which X represents an optionallysubstituted alkyl or phenyl radical (compounds of the formula Ic inScheme 4) can be prepared as shown in Scheme 4 starting with the esters(II) which are known from the literature (see, for example, U.S. Pat.No. 3,515,715 and U.S. Pat. No. 3,634,391), by reaction withβ-ketoesters of the formula XIV which are likewise known from theliterature or can be prepared by methods known from the literature (see,for example, EP-A 1 002 788):

Novel and thus likewise part of the subject-matter of the presentinvention is the reaction of the acid chlorides XIX with compounds ofthe formula VIII to give compounds of the formula Ic.

The synthesis of compounds of the formula (I) in which X represents amercapto, sulphinyl or sulphonyl group (compounds of the formula Id inScheme 5) is shown in Scheme 5 in an exemplary manner for compoundswhere X═S(O)₀₋₂—CH₃. Here, the cyanoalkenes can be prepared analogouslyto Gompper et al., Chem. Ber. 1962, 95, 2861-70 or Chauhan et al.,Tetrahedron 1976, 32, 1779-87.

Novel and thus likewise part of the subject-matter of the presentinvention is the reaction of the acid chlorides XXIV with compounds ofthe formula VIII to give compounds of the formula Id.

The synthesis of compounds of the formula (I) in which X represents ahydroxyl or an alkoxy group (compounds of the formula Ie in Scheme 6) isshown in Scheme 6 in an exemplary manner for compounds where X═OH andOCH₃.

Compounds of the formula V (in which R=Me) (=compounds of the formulaXXV, Scheme VII) can be reacted with methoxide (see, for example,Tetrahedron 1996, 52(5), 1735-46) to give methoxy compounds of theformula XXVI. According to methods known from the literature, thesecompounds are converted into the corresponding carboxylic acids XXVII.Analogously to Schemes 1/2, these are converted further via thecorresponding carbonyl chlorides into the corresponding amides.

The processes according to the invention for preparing the compounds ofthe formula (I) are preferably carried out using one or more reactionauxiliaries.

Suitable reaction auxiliaries are, if appropriate, the customaryinorganic or organic bases or acid acceptors. These preferably includealkali metal or alkaline earth metal acetates, amides, carbonates,bicarbonates, hydrides, hydroxides or alkoxides, such as, for example,sodium acetate, potassium acetate or calcium acetate, lithium amide,sodium amide, potassium amide or calcium amide, sodium carbonate,potassium carbonate or calcium carbonate, sodium bicarbonate, potassiumbicarbonate or calcium bicarbonate, lithium hydride, sodium hydride,potassium hydride or calcium hydride, lithium hydroxide, sodiumhydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide,ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassiummethoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide;furthermore also basic organic nitrogen compounds, such as, for example,trimethylamine, triethylamine, tripropylamine, tributylamine,ethyldiisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine,ethyldicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine,4-dimethylaminopyridine, N-methylpiperidine,1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene(DBN), or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The processes according to the invention are preferably carried outusing one or more diluents. Suitable diluents are virtually all inertorganic solvents. These preferably include aliphatic and aromatic,optionally halogenated hydrocarbons, such as pentane, hexane, heptane,cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene,xylene, methylene chloride, ethylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, ethers, such asdiethyl ether and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane, ketones, such as acetone,methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone,esters, such as methyl acetate or ethyl acetate, nitriles, such as, forexample, acetonitrile or propionitrile, amides, such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

The reaction temperatures in the processes according to the inventioncan be varied within a relatively wide range. In general, the processesare carried out at temperatures between 0° C. and 250° C., preferably attemperatures between 10° C. and 185° C.

The processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure.

For carrying out the processes according to the invention, the startingmaterials required in each case are generally employed in approximatelyequimolar amounts. However, it is also possible to use a relativelylarge excess of one of the components employed in each case. Work-up inthe processes according to the invention is in each case carried out bycustomary methods (cf. the Preparation Examples).

The compounds according to the invention have potent microbicidalactivity and can be employed for controlling unwanted microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

diseases caused by powdery mildew pathogens, such as, for example

Blumeria species such as, for example, Blumeria graminis;

Podosphaera species such as, for example, Podosphaera leucotricha;

Sphaerotheca species such as, for example, Sphaerotheca fuliginea;

Uncinula species such as, for example, Uncinula necator;

diseases caused by rust pathogens such as, for example,

Gymnosporangium species such as, for example, Gymnosporangium sabinae

Hemileia species such as, for example, Hemileia vastatrix;

Phakopsora species such as, for example, Phakopsora pachyrhizi andPhakopsora meibomiae;

Puccinia species such as, for example, Puccinia recondita;

Uromyces species such as, for example, Uromyces appendiculatus;

diseases caused by pathogens from the Oomycetene group such as, forexample,

Bremia species such as, for example, Bremia lactucae;

Peronospora species such as, for example, Peronospora pisi or P.brassicae;

Phytophthora species such as, for example, Phytophthora infestans;

Plasmopara species such as, for example, Plasmopara viticola;

Pseudoperonospora species such as, for example, Pseudoperonospora humulior Pseudoperonospora cubensis;

Pythium species such as, for example, Pythium ultimum;

leaf spot diseases and leaf wilts caused by, for example,

Alternaria species such as, for example, Alternaria solani;

Cercospora species such as, for example, Cercospora beticola;

Cladiosporum species such as, for example, Cladiosporium cucumerinum;

Cochliobolus species such as, for example, Cochliobolus sativus

(conidial form: Drechslera, syn: Helminthosporium);

Colletotrichum species such as, for example, Colletotrichumlindemuthanium;

Cycloconium species such as, for example, Cycloconium oleaginum;

Diaporthe species such as, for example, Diaporthe citri;

Elsinoe species such as, for example, Elsinoe fawcettii;

Gloeosporium species such as, for example, Gloeosporium laeticolor;

Glomerella species such as, for example, Glomerella cingulata;

Guignardia species such as, for example, Guignardia bidwelli;

Leptosphaeria species such as, for example, Leptosphaeria maculans;

Magnaporthe species such as, for example, Magnaporthe grisea;

Mycosphaerella species such as, for example, Mycosphaerelle graminicola;

Phaeosphaeria species such as, for example, Phaeosphaeria nodorum;

Pyrenophora species such as, for example, Pyrenophora teres;

Ramularia species such as, for example, Ramularia collo-cygni;

Rhynchosporium species such as, for example, Rhynchosporium secalis;

Septoria species such as, for example, Septoria apii;

Typhula species such as, for example, Typhula incamata;

Venturia species such as, for example, Venturia inaequalis;

root and stem diseases caused by, for example,

Corticium species such as, for example, Corticium graminearum;

Fusarium species such as, for example, Fusarium oxysporum;

Gaeumannomyces species such as, for example, Gaeumannomyces graminis;

Rhizoctonia species such as, for example, Rhizoctonia solani;

Tapesia species such as, for example, Tapesia acuformis;

Thielaviopsis species such as, for example, Thielaviopsis basicola;

ear and panicle diseases (including maize cobs), caused by, for example,

Alternaria species such as, for example, Alternaria spp.;

Aspergillus species such as, for example, Aspergillus flavus;

Cladosporium species such as, for example, Cladosporium spp.;

Claviceps species such as, for example, Claviceps purpurea;

Fusarium species such as, for example, Fusarium culmorum;

Gibberella species such as, for example, Gibberella zeae;

Monographella species such as, for example, Monographella nivalis;

diseases caused by smuts such as, for example,

Sphacelotheca species such as, for example, Sphacelotheca reiliana;

Tilletia species such as, for example, Tilletia caries;

Urocystis species such as, for example, Urocystis occulta;

Ustilago species such as, for example, Ustilago nuda;

fruit rots caused by, for example,

Aspergillus species such as, for example, Aspergillus flavus;

Botrytis species such as, for example, Botrytis cinerea;

Penicillium species such as, for example, Penicillium expansum;

Sclerotinia species such as, for example, Sclerotinia sclerotiorum;

Verticilium species such as, for example, Verticilium alboatrum;

seed- and soil-borne rot and wilts, and seedling diseases, caused by,for example,

Fusarium species such as, for example, Fusarium culmorum;

Phytophthora species such as, for example, Phytophthora cactorum;

Pythium species such as, for example, Pythium ultimum;

Rhizoctonia species such as, for example, Rhizoctonia solani;

Sclerotium species such as, for example, Sclerotium rolfsii;

cankers, galls and witches' broom disease, caused by, for example,

Nectria species such as, for example, Nectria galligena;

wilts caused by, for example,

Monilinia species such as, for example, Monilinia laxa;

deformations of leaves, flowers and fruits, caused by, for example,

Taphrina species such as, for example, Taphrina deformans;

degenerative diseases of woody species, caused by, for example,

Esca species such as, for example, Phaemoniella clamydospora;

diseases of inflorescences and seeds, caused by, for example,

Botrytis species such as, for example, Botrytis cinerea;

diseases of the plant tubers, caused by, for example,

Rhizoctonia species such as, for example, Rhizoctonia solani.

The following diseases of soybeans can preferably be controlled:

Fungal diseases on leaves, stems, pods and seeds caused by, for example,

alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose(Colletotrichum gloeosporoides dematium var. truncatum), brown spot(Septoria glycines), cercospora leaf spot and blight (Cercosporakikuchii), choanephora leaf blight (Choanephora infundibulifera trispora(syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew(Peronospora manshurica), drechslera blight (Drechslera glycini),frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot(Leptosphaerulina trifolii), phyllostica leaf spot (Phyllostictasojaecola), powdery mildew (Microsphaera diffusa), pyrenochaeta leafspot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and webblight (Rhizoctonia solani), rust (Phakopsora pachyrhizi), scab(Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum),target spot (Corynespora cassiicola);fungal diseases on roots and the stem base caused by, for example,black root rot (Calonectria crotalariae), charcoal rot (Macrophominaphaseolina), fusarium blight or wilt, root rot, and pod and collar rot(Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusariumequiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris),neocosmospora (Neocosmopspora vasinfecta), pod and stem blight(Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var.caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot(Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythiumirregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum),rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani),sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southernblight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsisbasicola).

The active compounds according to the invention also show a stronginvigorating action in plants. Accordingly, they are suitable formobilizing the internal defences of the plant against attack by unwantedmicroorganisms.

In the present context, plant-invigorating (resistance-inducing)compounds are to be understood as meaning substances which are capableof stimulating the defence system of plants such that, when the treatedplants are subsequently inoculated with unwanted microorganisms, theydisplay substantial resistance to these microorganisms.

In the present case, unwanted microorganisms are to be understood asmeaning phytopathogenic fungi and bacteria. The compounds according tothe invention can thus be used to protect plants within a certain periodof time after treatment against attack by the pathogens mentioned. Theperiod of time for which this protection is achieved generally extendsfor 1 to 10 days, preferably 1 to 7 days, from the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention can be employed withparticularly good results for controlling cereal diseases, such as, forexample, against Erysiphe species, and of diseases in viticulture and inthe cultivation of fruit and vegetables, such as, for example, againstBotrytis, Venturia, Sphaerotheca and Podosphaera species.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

If appropriate, the active compounds according to the invention can, atcertain concentrations and application rates, also be employed asherbicides, for regulating plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates orprecursors in the synthesis of other active compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations, such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested material and vegetative and generative propagation material,for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormultilayer coating.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, unwanted microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be tackifiers, sizes, paper and board, textiles,leather, wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably tackifiers, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,pumice, marble, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can, as such or in theirformulations, also be used in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Suitable mixing components are, for example, the following compounds:

Fungicides:

1. Nucleic Acid Synthesis Inhibitors

benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl-M, ofurace,oxadixyl, oxolinic acid

2. Mitosis and Cell Division Inhibitors

benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron,thiabendazole, thiophanate-methyl, zoxamide

3. Inhibitors of the Respiratory Chain

3.1 Complex I

diflumetorim

3.2 Complex II

boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil,oxycarboxin, penthiopyrad, thifluzamide

3.3 Complex III

azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone,fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin,orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin

3.4 Decouplers

dinocap, fluazinam

3.5 ATP production inhibitors

fentin acetate, fentin chloride, fentin hydroxide, silthiofam

4. Amino Acid and Protein Biosynthesis Inhibitors

andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim, pyrimethanil

5. Signal Transduction Inhibitors

fenpiclonil, fludioxonil, quinoxyfen

6. Lipid and Membrane Synthesis Inhibitors

chlozolinate, iprodione, procymidone, vinclozolin

pyrazophos, edifenphos, iprobenfos (IBP), isoprothiolane

tolclofos-methyl, biphenyl

iodocarb, propamocarb, propamocarb hydrochloride

7. Inhibitors of Ergosterol Biosynthesis

fenhexamid,

azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, epoxiconazole,etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole,metconazole, myclobutanil, paclobutrazol, penconazole, propiconazole,prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon,triadimenol, triticonazole, uniconazole, voriconazole, imazalil,imazalil sulphate, oxpoconazole, fenarimol, flurprimidol, nuarimol,pyrifenox, triforine, pefurazoate, prochloraz, triflumizole,viniconazole,

aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph,fenpropidin, spiroxamine,

naftifine, pyributicarb, terbinafine

8. Cell Wall Synthesis Inhibitors

benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb,polyoxins, polyoxorim, validamycin A

9. Melanin Biosynthesis Inhibitors

capropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole

10. Resistance Inductors

acibenzolar-S-methyl, probenazole, tiadinil

11. Compounds with Multisite Activity

captafol, captan, chlorothalonil, copper salts, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine copper and Bordeaux mixture, dichlofluanid,dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet,fosetyl-Al, guazatine, guazatine acetate, iminoctadine, iminoctadinealbesilate, iminoctadine triacetate, mancopper, mancozeb, maneb,metiram, metiram zinc, propineb, sulphur and sulphur preparationscomprising calcium polysulphide, thiram, tolylfluanid, zineb, ziram

12. Unknown

amibromdol, benthiazole, bethoxazin, capsimycin, carvone,chinomethionat, chloropicrin, cufraneb, cyflufenamid, cymoxanil,dazomet, debacarb, diclomezine, dichlorophen, dicloran, difenzoquat,difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone,flumetover, flusulfamide, fluopicolide, fluoroimide, hexachlorobenzene,8-hydroxyquinoline sulphate, irumamycin, methasulfocarb, metrafenone,methyl isothiocyanate, mildiomycin, natamycin, nickeldimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb,oxyfenthiin, pentachlorophenol and salts, 2-phenylphenol and salts,piperalin, propanosine-sodium, proquinazid, pyrrolnitrin, quintozene,tecloftalam, tecnazene, triazoxide, trichlamid, zarilamid and2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulphonamide,2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,3-triazol-3-one(185336-79-2), methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl2-[[[cyclopropyl-[(4-methoxyphenyl)imino]methyl]thio]methyl]-α-(methoxymethylene)benzylacetate,4-chloro-α-propynyloxy-N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]benzacetamide,(2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloronicotinamide,2-butoxy-6-iodo-3-propylbenzopyranon-4-one,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-benzacetamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide,2-[[[[1-[3-(1-fluoro-2-phenylethyl)oxy]phenyl]ethylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methyl-α-benzacetamide,N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide,1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylicacid,O-[1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1H-imidazole-1-carbothioicacid,2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

1. Acetylcholinesterase (AChE) Inhibitors

1.1 carbamates (for example alanycarb, aldicarb, aldoxycarb, allyxycarb,aminocarb, azamethiphos, bendiocarb, benfuracarb, bufencarb, butacarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilan,ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb,isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl,pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate,trimethacarb, XMC, xylylcarb)

1.2 organophosphates (for example acephate, azamethiphos, azinphos(-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl),butathiofos, cadusafos, carbophenothion, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos,cyanofenphos, cyanophos, chlorfenvinphos, demeton-s-methyl,demeton-s-methylsulphon, dialifos, diazinon, dichlofenthion,dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos,iprobenfos, isazofos, isofenphos, isopropyl o-salicylate, isoxathion,malathion, mecarbam, methacrifos, methamidophos, methidathion,mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion(-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon,phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos,propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion,pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos,temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,triclorfon, vamidothion)

2. Sodium Channel Modulators/Blockers of Voltage-Gated Sodium Channels

2.1 pyrethroids (for example acrinathrin, allethrin (d-cis-trans,d-trans), beta-cyfluthrin, bifenthrin, bioallethrin,bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin,bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin,cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin,cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT,deltamethrin, empenthrin (1R-isomer), esfenvalerate, etofenprox,fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate,flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox,gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin,metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans isomer),prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin,tetramethrin (1R-isomer), tralomethrin, transfluthrin, ZXI 8901,pyrethrins (pyrethrum))

2.2 oxadiazines (for example indoxacarb)

3. Acetylcholine Receptor Agonists/Antagonists

3.1 chloronicotinyls/neonicotinoids (for example acetamiprid,clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine,thiacloprid, thiamethoxam)

3.2 nicotine, bensultap, cartap

4. Acetylcholine Receptor Modulators

4.1 spinosyns (for example spinosad)

5. Antagonists of GABA-Gated Chloride Channels

5.1 cyclodiene organochlorines (for example camphechlor, chlordane,endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor)

5.2 fiproles (for example acetoprole, ethiprole, fipronil, vaniliprole)

6. Chloride Channel Activators

6.1 mectins (for example abamectin, avermectin, emamectin,emamectin-benzoate, ivermectin, milbemectin, milbemycin)

7. Juvenile Hormone Mimetics

(for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene,methoprene, pyriproxifen, triprene)

8. Ecdyson Agonists/Disruptors

8.1 diacylhydrazines (for example chromafenozide, halofenozide,methoxyfenozide, tebufenozide)

9. Chitin biosynthesis inhibitors

9.1 benzoylureas (for example bistrifluoron, chlofluazuron,diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron,lufenuron, novaluron, noviflumuron, penfluoron, teflubenzuron,triflumuron)

9.2 buprofezin

9.3 cyromazine

10. Inhibitors of Oxidative Phosphorylation, ATP Disruptors

10.1 diafenthiuron

10.2 organotins (for example azocyclotin, cyhexatin, fenbutatin-oxide)

11. Decouplers of Oxidative Phosphorylation Acting by Interrupting theH-Proton Gradient

11.1 pyrroles (for example chlorfenapyr)

11.2 dinitrophenols (for example binapacryl, dinobuton, dinocap, DNOC)

12. Site-I Electron Transport Inhibitors

12.1 METIs (for example fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad, tolfenpyrad)

12.2 hydramethylnone

12.3 dicofol

13. Site-II Electron Transport Inhibitors

13.1 rotenone

14. Site-III Electron Transport Inhibitors

14.1 acequinocyl, fluacrypyrim

15. Microbial Disruptors of the Insect Gut Membrane

Bacillus thuringiensis Strains

16. Inhibitors of Fat Synthesis

16.1 tetronic acids (for example spirodiclofen, spiromesifen)

16.2 tetramic acids [for example3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-ylethyl carbonate (alias: carbonic acid,3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-ylethyl ester, CAS Reg. No.: 382608-10-8) and carbonic acid,cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-ylethyl ester (CAS Reg. No.: 203313-25-1)]

17. Carboxamides

(for example flonicamid)

18. Octopaminergic Agonists

(for example amitraz)

19. Inhibitors of Magnesium-Stimulated ATPase

(for example propargite)

20. Phthalamides

(for exampleN²-[1,1-dimethyl-2-(methylsulphonyl)ethyl]-3-iodo-N¹-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide(CAS Reg. No.: 272451-65-7), flubendiamide)

21. Nereistoxin Analogues

(for example thiocyclam hydrogen oxalate, thiosultap-sodium)

22. Biologicals, Hormones or Pheromones

(for example azadirachtin, Bacillus spec., Beauveria spec., Codlemone,Metarrhizium spec., Paecilomyces spec., Thuringiensin, Verticilliumspec.)

23. Active Compounds with Unknown or Unspecific Mechanisms of Action

23.1 fumigants (for example aluminium phosphide, methyl bromide,sulphuryl fluoride)

23.2 selective antifeedants (for example cryolite, flonicamid,pymetrozine)

23.3 mite growth inhibitors (for example clofentezine, etoxazole,hexythiazox)

23.4 amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate,buprofezin, chinomethionat, chlordimeform, chlorobenzilate,chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil,fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin,gossyplure, hydramethylnone, japonilure, metoxadiazone, petroleum,piperonyl butoxide, potassium oleate, pyrafluprole, pyridalyl,pyriprole, sulfluramid, tetradifon, tetrasul, triarathene, verbutin,

furthermore the compound 3-methylphenyl propylcarbamate (Tsumacide Z),the compound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile(CAS Reg. No. 185982-80-3) and the corresponding 3-endo-isomer (CAS Reg.No. 185984-60-5) (cf. WO 96/37494, WO 98/25923), and preparations whichcomprise insecticidally active plant extracts, nematodes, fungi orviruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, safeners and/or semiochemicals isalso possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata) and Epidermophytonfloccosum, Aspergillus species such as Aspergillus niger and Aspergillusfumigatus, Trichophyton species such as Trichophyton mentagrophytes,Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi does by no means limit the mycotic spectrum which can becovered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10 000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10 000 g/ha, preferablybetween 1 and 5 000 g/ha.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof, are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are particularly emphasized are increased defence ofthe plants against insects, arachnids, nematodes and slugs and snails bytoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c,Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelowreferred to as “Bt plants”). Traits that are also particularlyemphasized are the increased defence of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned also include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars which have these genetic traits or genetic traitsstill to be developed, and which will be developed and/or marketed inthe future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The compounds of the formula (I) according to the invention arefurthermore suitable for suppressing the growth of tumour cells inhumans and mammals. This is based on an interaction of the compoundsaccording to the invention with tubulin and microtubuli and by promotingmicrotubuli polymerization.

Microtubuli play a key role in the regulation of the structure, themetabolism and the division of cells. Within the cells, tubulin ispolymerized in the microtubuli which form mitotic spindles. Themicrotubuli are depolymerized once the purpose of the mitotic spindleshas been accomplished. Active compounds which disrupt polymerization ordepolymerization of the microtubuli in neoplastic cells, thus inhibitingthe proliferation of these cells, belong to the most effectivechemotherapeutic anticancer agents currently available. The best-knownexamples of these are the discodermolides and epothilones (Nicolaou etal., Angew. Chem. 1998, 110, 2120-2153) and also paclitaxel (Taxol).

For this purpose, it is possible to administer an effective amount ofone or more compounds of the formula (I) or pharmaceutically acceptablesalts thereof.

Compounds of the formula (I) can be used for treating a large number oftypes of cancer and other proliferation diseases. Examples of suchdisorders are:

carcinomas, including carcinomas of the bladder, breast, colon, kidneys,liver, lungs, ovaries, pancreas, stomach, cervix, thyroid and skin,including squamous carcinomas;

haematopoetic tumours of the lymphoid cell line, including leukaemias,acute lymphocytic leukaemias, acute lymphoblastic leukaemias, B-celllymphomas, T-cell lymphomas, Hodgkin lymphomas, non-Hodgkin lymphomas,hairy cell lymphomas and Burketts lymphomas;

haematopoetic tumours of the myeloid cell line, including acute andchronic myelogenic leukaemias and promyelocytic leukaemias;

tumours of mesenchymal origin, including fibrosarcomas andrhabdomyosarcomas;

tumours of the central and peripheral nervous system, includingastrocytomas, neuroblastomas, gliomas and schwannomas;

tumours of mesenchymal origin, including fibrosarcomas,rhabdomyosarcomas and osteosarcomas; and

other tumours, including melanomas, seminomas, teratocarcinomas,neuroblastomas, gliomas, Xenoderma pigmentosum, keratoactanthomas andfollicular thyroid carcinomas.

The effective amount of a compound of the formula I can be determined bya person of average skill in the art and includes exemplary dosageamounts for a human of about 0.05 to 200 mg/kg/day which can beadministered in a single dose or in the form of individual separatedoses, such as 1 to 4 times per day. Preferably, the compounds areadministered in a dosage of less than 100 mg/kg/day, in a single dose orin 2 to 4 separate doses. It is evident that the specific dose and thedosage frequency for a certain patient can be varied and depend on alarge number of factors, including the effectiveness of the particularcompound used, the metabolic stability and the duration of action ofthis compound, the species, the age, the body weight, the general stateof health, the sex and the diet of the patient, the mode and the time ofadministration, the elimination rate, the medicament combination and theseverity of the particular disorder.

Thus, the present invention provides a medicament for humans whichcomprises at least one compound of the formula (I) and which allows thetreatment of cancer and other proliferation diseases, in an amounteffective in this context, and a pharmaceutically acceptable carrier ora pharmaceutically acceptable diluent. The compositions according to theinvention may comprise other therapeutic agents as described below andcan be formulated using, for example, customary solid or liquid carriersor diluents, such as pharmaceutical additives of a type suitable for thedesired administration (for example excipients, binders, preservatives,stabilizers, flavours, etc.), using techniques which are well known inthe field of pharmaceutical formulation or required by standardpharmaceutical practice.

The compounds of the formula I can be administered by any suitablemeans, for example orally, such as in the form of tablets, capsules,granules or powder, sublingually, buccally, parenterally, such as bysubcutaneous, intravenous, intramuscular or intrasternal injection orinfusion techniques (for example as sterile, injectable, aqueous ornon-aqueous solutions or suspensions), nasally, such as by means of aninhalation spray; topically, such as in the form of a cream or ointment,or rectally, such as in the form of suppositories, in dosage unitformulations comprising non-toxic pharmaceutically acceptable carriersor diluents. The compounds of the formula I can be administered, forexample, in a form suitable for immediate release or delayed release.Immediate release or delayed release can be achieved by using suitablemedicaments comprising the compounds of the formula I or, in particularin the case of a delayed release, by using devices such as subcutaneousimplants or osmotic pumps. The compounds of the formula I can also beadministered in liposomal form. The active substance can be used, forexample, in a composition such as a tablet, a capsule, a solution orsuspension comprising about 5 to about 500 mg per unit dose of acompound or a mixture of compounds of the formula or in a topical form(0.01 to 5% by weight of the compound of the formula I, one to fivetreatments per day). It can be mixed in a customary manner with aphysiologically acceptable carrier, excipient, binder, preservative,stabilizer, flavour, etc., or with a topical carrier. The compounds ofthe formula I can also be formulated in compositions, such as sterilesolutions or suspensions, for parenteral administration. About 0.1 to500 mg of a compound of the formula I can be mixed with aphysiologically acceptable carrier, excipient, binder, preservative,stabilizer, etc., in a unit dosage form, as required by standardpharmaceutical practice. The amount of active substance in thesecompositions or preparations is preferably such that a suitable dosagein the stated range is obtained.

Exemplary compositions for oral administration include suspensions whichmay comprise, for example, microcrystalline cellulose to increase thebulk, alginic acid or sodium alginate as suspending agent,methylcellulose as viscosity-increasing agent, and sweeteners orflavours such as those known in the art, and tablets with immediaterelease which may, for example, comprise microcrystalline cellulose,dicalcium phosphate, starch, magnesium stearate and/or lactose and/orother excipients, binders, extenders, peptizers, diluents and glidants,such as those known in the art. Formed tablets, pressed tablets orfreeze-dried tablets are exemplary forms which may be used. Exemplarycompositions include those which formulate the compounds of the formulaI with rapidly soluble solvents, such as mannitol, lactose, sucroseand/or cyclodextrins. Such formulations may also comprise excipients ofhigh molecular weight, such as celluloses (Avicel) or polyethyleneglycols (PEG). Such formulations may also contain an excipient tosupport adhesion to the mucosa, such as hydroxypropylcellulose (HPC),hydroxypropylmethylcellulose (HPMC), sodium carboxymethylcellulose(SCMC), maleic anhydride copolymers (for example Gantrez) and agents forcontrolling the release, such as polyacrylate copolymer (for exampleCarbopol 934). Lubricants, glidants, flavours, colorants and stabilizersmay also be added, to facilitate preparation and use.

Exemplary compositions for nasal aerosol and inhalation administrationinclude solutions in physiological saline comprising, for example,benzyl alcohol and other suitable preservatives, absorption enhancers toincrease the bioavailability and/or other solubilizers and dispersants,such as those known in the art.

Exemplary compositions for parenteral administration include injectablesolutions or suspensions which may comprise, for example, suitablenon-toxic parenterally acceptable diluents or solvents, such asCremophor, mannitol, 1,3-butanediol, water, Ringer solution, an isotonicsodium chloride solution or other dispersants; or wetting agents andsuspension agents, including synthetic mono- or diglycerides, and fattyacids, including oleic acids.

Exemplary compositions for rectal administration include suppositorieswhich may contain, for example, a suitable non-irritating excipient,such as cocoa butter, synthetic glyceride esters or polyethyleneglycols, which are solid at normal temperature but liquefy and/ordissolve in the rectal cavity, releasing the medicament.

Exemplary compositions for topical administration include a topicalcarrier, such as Plastibase (mineral oil gelated with polyethylene). Thecompounds of the formula I can be administered topically to treat theplaques associated with psoriasis, for example, and can be formulated assuch as a cream or ointment.

The compounds of the formula I can be administered either on their ownor in combination with other anticancer and cytotoxic agents andtreatments suitable for managing cancer or other proliferationdisorders. Particularly useful are anticancer and cytotoxic medicamentcombinations in which the second chosen medicament acts in a differentmanner or during a different phase of the cell cycle, for example the Sphase, than the present compounds of the formula I which are activeduring the G2-M phase. Examples of classes of anticancer and cytotoxicagents include alkylating agents, such as nitrogen mustard,alkylsulphonates, nitrosoureas, ethyleneimines and triazenes;antimetabolites, such as folate antagonists, purine analogues andpyrimidine analogues; antibiotics, such as anthracyclines, bleomycins,mitomycin, dactinomycin and plicamycin; enzymes, such as L-aspartase;farnesyl protein transferase inhibitors; hormonal agents, such asglucocorticoids, oestrogens/anti-oestrogens, androgens/antiandrogens,progestins and luteinizing hormone-releasing hormone antagonists,octreotide acetate; microtubulus-destroying agents, such asectein-ascidins or their analogues and derivatives;microtubulus-stabilizing agents, such as paclitaxel (Taxol), docetaxel(Taxotere) and epothilones A-F or their analogues or derivatives;plant-derived products, such as vinca alkaloids, epipodophyllotoxins,taxanes; and topoisomerase inhibitors; prenyl protein transferaseinhibitors; and various agents, such as hydroxyurea, procarbazine,mitotane, hexamethylmelamine, platinum coordination complexes, such ascisplatin and carboplatin; and other agents used as anticancer andcytotoxic agents, such as agents which modify the biological reaction,growth factors, immunomodulators and monoclonal antibodies. Thecompounds of the formula I can also be used in combination withradiotherapy.

Representative examples of these classes of anticancer and cytotoxicagents include mechlorethamine hydrochloride, cyclophosphamid,chlorambucil, melphalan, ifosfamid, busulfan, carmustine, lomustine,semustine, streptozocin, thiotepa, dacarbazin, methotrexate,thioguanine, mercaptopurine, fludarabine, pentastatin, cladribin,cytarabine, fluorouracil, doxorubicin hydrochloride, daunorubicin,idarubicin, bleomycin sulphate, mitomycin C, actinomycin D, safracins,saframycins, quinocarcins, discodermolides, vincristine, vinblastine,vinorelbine tartrate, etoposide, teniposide, paclitaxel, tamoxifen,estramustine, estramustine phosphate sodium, flutamide, buserelin,leuprolide, pteridines, diyneses, levamisole, aflacon, interferon,interleukins, aldesleukin, filgrastim, sargramostim, rituximab, BCG,tretinoin, irinotecan hydrochloride, betamethasone, gemcitabinehydrochloride, altretamine and topoteca and all analogues or derivativesthereof.

Preferred members of these classes include paclitaxel, cisplatin,carboplatin, doxorubicin, caminomycin, daunorubicin, aminopterin,methotrexate, methopterin, mitomycin C, ecteinascidin 743, porfiromycin,5-fluorouracil, mercaptopurine, gemcitabine, cytosine arabinoside,podophyllotoxin or podophyllotoxin derivatives, such as etoposide,etoposide phosphate or teniposide, melphalan, vinblastine, vincristine,leurosidine, vindesine and leurosine.

The combinations of the present invention can also be formulated oradministered together with other therapeutic agents selected by virtueof their particular usefulness in the administration of therapiesassociated with the disorders listed above. The compounds of the formulaI can be formulated, for example, with agents such as antiemetics and H1and H2 antihistamines, to prevent nausea, hypersensitivity and stomachirritations.

When used in combination with the compounds of the formula I, thetherapeutic agents listed above can be administered in the amountsstated in the Physicians' Desk Reference (PDR) or otherwise determinedby a person of average skill.

Novel and thus likewise part of the subject-matter of the presentinvention is the use of compounds of the formula I as medicaments.

Furthermore novel and thus likewise part of the subject-matter of thepresent invention is the use of compounds of the formula I for preparingmedicaments, in particular medicaments against cancer.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

EXAMPLES Example IN-[5-Chloro-6-(2,4-dichlorophenyl)-7-isopropylaminopyrazolo[1,5-a]pyrimidine-3-carbonyl]methanesulphonamide

0.95 g of oxalyl chloride and a drop of dimethylformamide were added toa solution of 1 g of5-chloro-6-(2,4-dichlorophenyl)-7-isopropylaminopyrazolo[1,5-a]pyrimidine-3-carboxylicacid in 20 ml of dichloromethane, and the mixture was stirred until theevolution of gas had ceased. The mixture was then concentrated and takenup again in dichloroethane (5 ml). A solution of 126 mg ofmethanesulphonamide in 1 ml of pyridine was added dropwise to theresulting solution. After further stirring at room temperature, duringwhich the reaction was monitored by TLC, the reaction was quenched with1N hydrochloric acid, the mixture was concentrated and the residue waspurified chromatographically using n-hexane/ethyl acetate 5:1→3:1. Thisgave 0.029 g ofN-[5-chloro-6-(2,4-dichlorophenyl)-7-isopropylaminopyrazolo[1,5-a]pyrimidine-3-carbonyl]methanesulphonamide(5% of theory).

The compounds of the formula (I-a) listed in Table 1 below are or werealso obtained analogously to the methods described above.

TABLE 1

R¹ R² Ex. or No. —R¹⁺R²— R3 X R4 log p  1 CH(CH₃)—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHCONHCH₃  2 CH(CH₃)—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHSO₂CF₃  3 (R) CH(CH₃)—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 4.19*  4 CH(CH₃)—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃  5 CH(CH₃)—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl  6CH(CH₃)—C(CH₃)₃ H 2-chloro-6-fluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl  7 CH(CH₃)—C(CH₃)₃ H2,4,6-trifluorophenyl Cl CONHCONHCH₃  8 CH(CH₃)—C(CH₃)₃ H2,4,6-trifluorophenyl Cl CONHSO₂CF₃  9 (R) CH(CH₃)—C(CH₃)₃ H2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 4.16  10 CH(CH₃)—C(CH₃)₃ H2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃  11 CH(CH₃)—C(CH₃)₃ H2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl  12CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl  13 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl Cl CONHCONHCH₃  14 (R) CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl Cl CONHSO₂CF₃ 3.77  15 (R) CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 4.44  16 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃  17 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl  18CH(CH₃)—C(CH₃)₃ H 2-chloro-4-fluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl  19 CH(CH₃)—C(CH₃)₃ H2-chlorophenyl Cl CONHCONHCH₃  20 CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl ClCONHSO₂CF₃  21 (R) CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl Cl CONHSO₂CH₃ 4.36* 22 CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl Cl CONHSO₂CH₂CH₃  23CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl  24CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl  25 CH(CH₃)—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl ClCONHCONHCH₃  26 CH(CH₃)—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃  27CH(CH₃)—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃  28 CH(CH₃)—C(CH₃)₃H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃  29 CH(CH₃)—C(CH₃)₃ H5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl  30 CH(CH₃)—C(CH₃)₃H 5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl  31 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- Cl CONHCONHCH₃difluorophenyl  32 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- Cl CONHSO₂CF₃difluorophenyl  33 (R) CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- Cl CONHSO₂CH₃4.38 difluorophenyl  34 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- Cl CONHSO₂CH₂CH₃difluorophenyl  35 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- Cl(isoxazol-3-ylamino)carbonyl difluorophenyl  36 CH(CH₃)—C(CH₃)₃ H2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl  37 CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl ClCONHCONHCH₃  38 (R) CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl Cl CONHSO₂CF₃3.93  39 (R) CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl Cl CONHSO₂CH₃ 4.89* 40 CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃  41CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl Cl (isoxazol-3-ylamino)carbonyl  42CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl  43 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- Cl CONHCONHCH₃difluorophenyl  44 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- Cl CONHSO₂CF₃difluorophenyl  45 (R) CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- Cl CONHSO₂CH₃4.55* difluorophenyl  46 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- ClCONHSO₂CH₂CH₃ difluorophenyl  47 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- Cl(isoxazol-3-ylamino)carbonyl difluorophenyl  48 CH(CH₃)—C(CH₃)₃ H4-chloro-2,6- Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl  49 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- Cl CONHCONHCH₃methylphenyl  50 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- Cl CONHSO₂CF₃methylphenyl  51 (R) CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- Cl CONHSO₂CH₃4.38** methylphenyl  52 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- ClCONHSO₂CH₂CH₃ methylphenyl  53 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- Cl(isoxazol-3-ylamino)carbonyl methylphenyl  54 CH(CH₃)—C(CH₃)₃ H2,6-difluoro-4- Cl [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl  55 CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl ClCONHCONHCH₃  56 CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 57 CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃  58CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃  59CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl  60 CH(CH₃)—C(CH₃)₃ H2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl  61 CH(CH₃)—C(CH₃)₃ H 3-chloro-2-thienyl ClCONHCONHCH₃  62 CH(CH₃)—C(CH₃)₃ H 3-chloro-2-thienyl Cl CONHSO₂CF₃  63CH(CH₃)—C(CH₃)₃ H 3-chloro-2-thienyl Cl CONHSO₂CH₃  64 CH(CH₃)—C(CH₃)₃ H3-chloro-2-thienyl Cl CONHSO₂CH₂CH₃  65 CH(CH₃)—C(CH₃)₃ H3-chloro-2-thienyl Cl (isoxazol-3-ylamino)carbonyl  66 CH(CH₃)—C(CH₃)₃ H3-chloro-2-thienyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 67 CH(CH₃)—C(CH₃)₃ H phenyl Cl CONHCONHCH₃  68 CH(CH₃)—C(CH₃)₃ H phenylCl CONHSO₂CF₃  69 CH(CH₃)—C(CH₃)₃ H phenyl Cl CONHSO₂CH₃  70CH(CH₃)—C(CH₃)₃ H phenyl Cl CONHSO₂CH₂CH₃  71 CH(CH₃)—C(CH₃)₃ H phenylCl (isoxazol-3-ylamino)carbonyl 4.88**  72 CH(CH₃)—C(CH₃)₃ H phenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl  73 CH(CH₃)—C(CH₃)₃ Hcyclopentyl Cl CONHCONHCH₃  74 CH(CH₃)—C(CH₃)₃ H cyclopentyl ClCONHSO₂CF₃  75 CH(CH₃)—C(CH₃)₃ H cyclopentyl Cl CONHSO₂CH₃  76CH(CH₃)—C(CH₃)₃ H cyclopentyl Cl CONHSO₂CH₂CH₃  77 CH(CH₃)—C(CH₃)₃ Hcyclopentyl Cl (isoxazol-3-ylamino)carbonyl  78 CH(CH₃)—C(CH₃)₃ Hcyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl  79CH(CH₃)—C(CH₃)₃ H sec-butyl Cl CONHCONHCH₃  80 CH(CH₃)—C(CH₃)₃ Hsec-butyl Cl CONHSO₂CF₃  81 CH(CH₃)—C(CH₃)₃ H sec-butyl Cl CONHSO₂CH₃ 82 CH(CH₃)—C(CH₃)₃ H sec-butyl Cl CONHSO₂CH₂CH₃  83 CH(CH₃)—C(CH₃)₃ Hsec-butyl Cl (isoxazol-3-ylamino)carbonyl  84 CH(CH₃)—C(CH₃)₃ Hsec-butyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl  85CH(CH₃)(CF₃) H 2-chloro-6-fluorophenyl Cl CONHCONHCH₃  86 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl Cl CONHSO₂CF₃  87 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl Cl CONHSO₂CH₃  88 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃  89 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl  90 CH(CH₃)(CF₃)H 2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl  91 CH(CH₃)(CF₃) H 2,4,6-trifluorophenyl ClCONHCONHCH₃  92 CH(CH₃)(CF₃) H 2,4,6-trifluorophenyl Cl CONHSO₂CF₃  93CH(CH₃)(CF₃) H 2,4,6-trifluorophenyl Cl CONHSO₂CH₃  94 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃  95 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl  96 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl  97 CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl ClCONHCONHCH₃  98 CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl Cl CONHSO₂CF₃  99CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 100 CH(CH₃)(CF₃) H2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃ 101 CH(CH₃)(CF₃) H2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 102 CH(CH₃)(CF₃)H 2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 103 CH(CH₃)(CF₃) H 2-chlorophenyl Cl CONHCONHCH₃ 104CH(CH₃)(CF₃) H 2-chlorophenyl Cl CONHSO₂CF₃ 105 CH(CH₃)(CF₃) H2-chlorophenyl Cl CONHSO₂CH₃ 106 CH(CH₃)(CF₃) H 2-chlorophenyl ClCONHSO₂CH₂CH₃ 107 CH(CH₃)(CF₃) H 2-chlorophenyl Cl(isoxazol-3-ylamino)carbonyl 108 CH(CH₃)(CF₃) H 2-chlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 109 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl Cl CONHCONHCH₃ 110 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃ 111 CH(CH₃)(CF₃) H 5-Cl-pyrimidin-4-ylCl CONHSO₂CH₃ 112 CH(CH₃)(CF₃) H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃113 CH(CH₃)(CF₃) H 5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl114 CH(CH₃)(CF₃) H 5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 115 CH(CH₃)(CF₃) H 2-chloro-4,6- Cl CONHCONHCH₃difluorophenyl 116 CH(CH₃)(CF₃) H 2-chloro-4,6- Cl CONHSO₂CF₃difluorophenyl 117 (S) CH(CH₃)(CF₃) H 2-chloro-4,6- Cl CONHSO₂CH₃ 3.56*difluorophenyl 118 CH(CH₃)(CF₃) H 2-chloro-4,6- Cl CONHSO₂CH₂CH₃difluorophenyl 119 CH(CH₃)(CF₃) H 2-chloro-4,6- Cl(isoxazol-3-ylamino)carbonyl difluorophenyl 120 CH(CH₃)(CF₃) H2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 121 CH(CH₃)(CF₃) H 2,4-dichlorophenyl Cl CONHCONHCH₃122 CH(CH₃)(CF₃) H 2,4-dichlorophenyl Cl CONHSO₂CF₃ 123 (S) CH(CH₃)(CF₃)H 2,4-dichlorophenyl Cl CONHSO₂CH₃ 3.99 124 CH(CH₃)(CF₃) H2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 125 CH(CH₃)(CF₃) H2,4-dichlorophenyl Cl (isoxazol-3-ylamino)carbonyl 126 CH(CH₃)(CF₃) H2,4-dichlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl127 CH(CH₃)(CF₃) H 4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 128CH(CH₃)(CF₃) H 4-chloro-2,6- Cl CONHSO₂CF₃ difluorophenyl 129CH(CH₃)(CF₃) H 4-chloro-2,6- Cl CONHSO₂CH₃ difluorophenyl 130CH(CH₃)(CF₃) H 4-chloro-2,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 131CH(CH₃)(CF₃) H 4-chloro-2,6- Cl (isoxazol-3-ylamino)carbonyldifluorophenyl 132 CH(CH₃)(CF₃) H 4-chloro-2,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 133CH(CH₃)(CF₃) H 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl 134CH(CH₃)(CF₃) H 2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl 135CH(CH₃)(CF₃) H 2,6-difluoro-4- Cl CONHSO₂CH₃ methylphenyl 136CH(CH₃)(CF₃) H 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃ methylphenyl 137CH(CH₃)(CF₃) H 2,6-difluoro-4- Cl (isoxazol-3-ylamino)carbonylmethylphenyl 138 CH(CH₃)(CF₃) H 2,6-difluoro-4- Cl[(4-methyl-4H-1,2,4-triazol-3- methylphenyl yl)amino]carbonyl 139CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl Cl CONHCONHCH₃ 140 CH(CH₃)(CF₃) H2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 141 CH(CH₃)(CF₃) H2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 142 CH(CH₃)(CF₃) H2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 143 CH(CH₃)(CF₃) H2-chloro-5-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 144 CH(CH₃)(CF₃)H 2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 145 CH(CH₃)(CF₃) H 3-chloro-2-thienyl Cl CONHCONHCH₃146 CH(CH₃)(CF₃) H 3-chloro-2-thienyl Cl CONHSO₂CF₃ 147 CH(CH₃)(CF₃) H3-chloro-2-thienyl Cl CONHSO₂CH₃ 148 CH(CH₃)(CF₃) H 3-chloro-2-thienylCl CONHSO₂CH₂CH₃ 149 CH(CH₃)(CF₃) H 3-chloro-2-thienyl Cl(isoxazol-3-ylamino)carbonyl 150 CH(CH₃)(CF₃) H 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 151 CH(CH₃)(CF₃) Hphenyl Cl CONHCONHCH₃ 152 CH(CH₃)(CF₃) H phenyl Cl CONHSO₂CF₃ 153CH(CH₃)(CF₃) H phenyl Cl CONHSO₂CH₃ 154 CH(CH₃)(CF₃) H phenyl ClCONHSO₂CH₂CH₃ 155 CH(CH₃)(CF₃) H phenyl Cl (isoxazol-3-ylamino)carbonyl156 CH(CH₃)(CF₃) H phenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 157 CH(CH₃)(CF₃) H cyclopentyl Cl CONHCONHCH₃ 158CH(CH₃)(CF₃) H cyclopentyl Cl CONHSO₂CF₃ 159 CH(CH₃)(CF₃) H cyclopentylCl CONHSO₂CH₃ 160 CH(CH₃)(CF₃) H cyclopentyl Cl CONHSO₂CH₂CH₃ 161CH(CH₃)(CF₃) H cyclopentyl Cl (isoxazol-3-ylamino)carbonyl 162CH(CH₃)(CF₃) H cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 163 CH(CH₃)(CF₃) H sec-butyl Cl CONHCONHCH₃ 164CH(CH₃)(CF₃) H sec-butyl Cl CONHSO₂CF₃ 165 CH(CH₃)(CF₃) H sec-butyl ClCONHSO₂CH₃ 166 CH(CH₃)(CF₃) H sec-butyl Cl CONHSO₂CH₂CH₃ 167CH(CH₃)(CF₃) H sec-butyl Cl (isoxazol-3-ylamino)carbonyl 168CH(CH₃)(CF₃) H sec-butyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 169 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl ClCONHCONHCH₃ 170 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl Cl CONHSO₂CF₃171 (R) CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 3.9*172 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 173CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 174 CH(CH₃)—CH(CH₃)₂ H2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 175 CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl ClCONHCONHCH₃ 176 CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl Cl CONHSO₂CF₃177 (R) CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 3.85* 178CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 179CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl180 CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 181 CH(CH₃)—CH(CH₃)₂ H2-chloro-4-fluorophenyl Cl CONHCONHCH₃ 182 CH(CH₃)—CH(CH₃)₂ H2-chloro-4-fluorophenyl Cl CONHSO₂CF₃ 183 (R) CH(CH₃)—CH(CH₃)₂ H2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 4.18 184 CH(CH₃)—CH(CH₃)₂ H2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃ 185 CH(CH₃)—CH(CH₃)₂ H2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 186CH(CH₃)—CH(CH₃)₂ H 2-chloro-4-fluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 187 CH(CH₃)—CH(CH₃)₂ H2-chlorophenyl Cl CONHCONHCH₃ 188 CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl ClCONHSO₂CF₃ 189 (R) CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl Cl CONHSO₂CH₃ 4.01*190 CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 191CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl 192CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 193 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl ClCONHCONHCH₃ 194 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃ 195CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃ 196CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 197CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl198 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 199 CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- Cl CONHCONHCH₃ difluorophenyl 200 CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl 201 (R) CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- Cl CONHSO₂CH₃ 4.05* difluorophenyl 202 CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 203 CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 204CH(CH₃)—CH(CH₃)₂ H 2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3-difluorophenyl yl)amino]carbonyl 205 CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl Cl CONHCONHCH₃ 206 (R) CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl Cl CONHSO₂CF₃ 3.87** 207 (R) CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl Cl CONHSO₂CH₃ 4.55* 208 (R) CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 4.88** 209 CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl Cl (isoxazol-3-ylamino)carbonyl 210 CH(CH₃)—CH(CH₃)₂H 2,4-dichlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl211 CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 212CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- Cl CONHSO₂CF₃ difluorophenyl 213 (R)CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- Cl CONHSO₂CH₃ 4.24* difluorophenyl 214CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 215CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- Cl (isoxazol-3-ylamino)carbonyldifluorophenyl 216 CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 217CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl 218CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl 219 (R)CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- Cl CONHSO₂CH₃ 4.08** methylphenyl 220CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃ methylphenyl 221CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- Cl (isoxazol-3-ylamino)carbonylmethylphenyl 222 CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- Cl[(4-methyl-4H-1,2,4-triazol-3- methylphenyl yl)amino]carbonyl 223CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl Cl CONHCONHCH₃ 224CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 225CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 226CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 227CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 228 CH(CH₃)—CH(CH₃)₂ H2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 229 CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl ClCONHCONHCH₃ 230 CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl Cl CONHSO₂CF₃ 231CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl Cl CONHSO₂CH₃ 232 CH(CH₃)—CH(CH₃)₂H 3-chloro-2-thienyl Cl CONHSO₂CH₂CH₃ 233 CH(CH₃)—CH(CH₃)₂ H3-chloro-2-thienyl Cl (isoxazol-3-ylamino)carbonyl 234 CH(CH₃)—CH(CH₃)₂H 3-chloro-2-thienyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl235 CH(CH₃)—CH(CH₃)₂ H phenyl Cl CONHCONHCH₃ 236 CH(CH₃)—CH(CH₃)₂ Hphenyl Cl CONHSO₂CF₃ 237 CH(CH₃)—CH(CH₃)₂ H phenyl Cl CONHSO₂CH₃ 238CH(CH₃)—CH(CH₃)₂ H phenyl Cl CONHSO₂CH₂CH₃ 239 CH(CH₃)—CH(CH₃)₂ H phenylCl (isoxazol-3-ylamino)carbonyl 240 CH(CH₃)—CH(CH₃)₂ H phenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 241 CH(CH₃)—CH(CH₃)₂ Hcyclopentyl Cl CONHCONHCH₃ 242 CH(CH₃)—CH(CH₃)₂ H cyclopentyl ClCONHSO₂CF₃ 243 CH(CH₃)—CH(CH₃)₂ H cyclopentyl Cl CONHSO₂CH₃ 244CH(CH₃)—CH(CH₃)₂ H cyclopentyl Cf CONHSO₂CH₂CH₃ 245 CH(CH₃)—CH(CH₃)₂ Hcyclopentyl Cl (isoxazol-3-ylamino)carbonyl 246 CH(CH₃)—CH(CH₃)₂ Hcyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 247CH(CH₃)—CH(CH₃)₂ H sec-butyl Cl CONHCONHCH₃ 248 CH(CH₃)—CH(CH₃)₂ Hsec-butyl Cl CONHSO₂CF₃ 249 CH(CH₃)—CH(CH₃)₂ H sec-butyl Cl CONHSO₂CH₃250 CH(CH₃)—CH(CH₃)₂ H sec-butyl Cl CONHSO₂CH₂CH₃ 251 CH(CH₃)—CH(CH₃)₂ Hsec-butyl Cl (isoxazol-3-ylamino)carbonyl 252 CH(CH₃)—CH(CH₃)₂ Hsec-butyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 253—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl Cl CONHCONHCH₃ 254—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl Cl CONHSO₂CF₃ 255—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 4.2* 256—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 257—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 258 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 259 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl ClCONHCONHCH₃ 260 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl ClCONHSO₂CF₃ 261 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl ClCONHSO₂CH₃ 4.07* 262 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl ClCONHSO₂CH₂CH₃ 263 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl Cl(isoxazol-3-ylamino)carbonyl 264 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 265 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenylCl CONHCONHCH₃ 266 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenyl ClCONHSO₂CF₃ 267 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenyl ClCONHSO₂CH₃ 268 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenyl ClCONHSO₂CH₂CH₃ 269 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 270 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 271 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl ClCONHCONHCH₃ 272 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl Cl CONHSO₂CF₃273 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl Cl CONHSO₂CH₃ 274—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 275—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl276 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 277—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHCONHCH₃ 278—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃ 279—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃ 280—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 281—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl(isoxazol-3-ylamino)carbonyl 282 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl283 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- Cl CONHCONHCH₃difluorophenyl 284 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- Cl CONHSO₂CF₃difluorophenyl 285 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- Cl CONHSO₂CH₃4.34* difluorophenyl 286 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- ClCONHSO₂CH₂CH₃ difluorophenyl 287 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6-Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 288—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 289—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl Cl CONHCONHCH₃ 290—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl Cl CONHSO₂CF₃ 291—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl Cl CONHSO₂CH₃ 292—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 293—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl Cl(isoxazol-3-ylamino)carbonyl 294 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2,4-dichlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl295 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- Cl CONHCONHCH₃difluorophenyl 296 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- Cl CONHSO₂CF₃difluorophenyl 297 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- Cl CONHSO₂CH₃difluorophenyl 298 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- ClCONHSO₂CH₂CH₃ difluorophenyl 299 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6-Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 300—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 301—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl302 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl303 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- Cl CONHSO₂CH₃ methylphenyl304 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃methylphenyl 305 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- Cl(isoxazol-3-ylamino)carbonyl methylphenyl 306 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2,6-difluoro-4- Cl [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl 307 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenylCl CONHCONHCH₃ 308 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl ClCONHSO₂CF₃ 309 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl ClCONHSO₂CH₃ 310 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl ClCONHSO₂CH₂CH₃ 311 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 312 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 313 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl ClCONHCONHCH₃ 314 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl ClCONHSO₂CF₃ 315 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl ClCONHSO₂CH₃ 316 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl ClCONHSO₂CH₂CH₃ 317 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl Cl(isoxazol-3-ylamino)carbonyl 318 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—3-chloro-2-thienyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl319 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl Cl CONHCONHCH₃ 320—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl Cl CONHSO₂CF₃ 321—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl Cl CONHSO₂CH₃ 322—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl Cl CONHSO₂CH₂CH₃ 323—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl Cl (isoxazol-3-ylamino)carbonyl 324—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 325 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl ClCONHCONHCH₃ 326 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl Cl CONHSO₂CF₃ 327—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl Cl CONHSO₂CH₃ 328—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl Cl CONHSO₂CH₂CH₃ 329—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl Cl (isoxazol-3-ylamino)carbonyl330 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 331—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl Cl CONHCONHCH₃ 332—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl Cl CONHSO₂CF₃ 333—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl Cl CONHSO₂CH₃ 334—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl Cl CONHSO₂CH₂CH₃ 335—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl Cl (isoxazol-3-ylamino)carbonyl 336—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 337 i-propyl H 2-chloro-6-fluorophenyl Cl CONHCONHCH₃338 i-propyl H 2-chloro-6-fluorophenyl Cl CONHSO₂CF₃ 339 i-propyl H2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 340 i-propyl H2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 341 i-propyl H2-chloro-6-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 342 i-propyl H2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 343 i-propyl H 2,4,6-trifluorophenyl Cl CONHCONHCH₃344 i-propyl H 2,4,6-trifluorophenyl Cl CONHSO₂CF₃ 345 i-propyl H2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 3.24* 346 i-propyl H2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 347 i-propyl H2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl 348 i-propyl H2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 349 i-propyl H 2-chloro-4-fluorophenyl Cl CONHCONHCH₃350 i-propyl H 2-chloro-4-fluorophenyl Cl CONHSO₂CF₃ 351 i-propyl H2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 3.57* 352 i-propyl H2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃ 353 i-propyl H2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 354 i-propyl H2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 355 i-propyl H 2-chlorophenyl Cl CONHCONHCH₃ 356i-propyl H 2-chlorophenyl Cl CONHSO₂CF₃ 357 i-propyl H 2-chlorophenyl ClCONHSO₂CH₃ 3.44* 358 i-propyl H 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 359i-propyl H 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl 360 i-propyl H2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 361i-propyl H 5-Cl-pyrimidin-4-yl Cl CONHCONHCH₃ 362 i-propyl H5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃ 363 i-propyl H 5-Cl-pyrimidin-4-yl ClCONHSO₂CH₃ 364 i-propyl H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 365i-propyl H 5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl 366i-propyl H 5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 367 i-propyl H 2-chloro-4,6- Cl CONHCONHCH₃difluorophenyl 368 i-propyl H 2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl369 i-propyl H 2-chloro-4,6- Cl CONHSO₂CH₃ difluorophenyl 370 i-propyl H2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 371 i-propyl H2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 372i-propyl H 2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3-difluorophenyl yl)amino]carbonyl 373 i-propyl H 2,4-dichlorophenyl ClCONHCONHCH₃ 374 i-propyl H 2,4-dichlorophenyl Cl CONHSO₂CF₃ 375 i-propylH 2,4-dichlorophenyl Cl CONHSO₂CH₃ 3.91* 376 i-propyl H2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 377 i-propyl H 2,4-dichlorophenyl Cl(isoxazol-3-ylamino)carbonyl 378 i-propyl H 2,4-dichlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 379 i-propyl H4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 380 i-propyl H 4-chloro-2,6-Cl CONHSO₂CF₃ difluorophenyl 381 i-propyl H 4-chloro-2,6- Cl CONHSO₂CH₃3.68* difluorophenyl 382 i-propyl H 4-chloro-2,6- Cl CONHSO₂CH₂CH₃difluorophenyl 383 i-propyl H 4-chloro-2,6- Cl(isoxazol-3-ylamino)carbonyl difluorophenyl 384 i-propyl H 4-chloro-2,6-Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 385i-propyl H 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl 386 i-propyl H2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl 387 i-propyl H2,6-difluoro-4- Cl CONHSO₂CH₃ methylphenyl 388 i-propyl H2,6-difluoro-4- Cl CONHSO₂CH₂CH₃ methylphenyl 389 i-propyl H2,6-difluoro-4- Cl (isoxazol-3-ylamino)carbonyl methylphenyl 390i-propyl H 2,6-difluoro-4- Cl [(4-methyl-4H-1,2,4-triazol-3-methylphenyl yl)amino]carbonyl 391 i-propyl H 2-chloro-5-fluorophenyl ClCONHCONHCH₃ 392 i-propyl H 2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 393i-propyl H 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 394 i-propyl H2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 395 i-propyl H2-chloro-5-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 396 i-propyl H2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 397 i-propyl H 3-chloro-2-thienyl Cl CONHCONHCH₃ 398i-propyl H 3-chloro-2-thienyl Cl CONHSO₂CF₃ 399 i-propyl H3-chloro-2-thienyl Cl CONHSO₂CH₃ 400 i-propyl H 3-chloro-2-thienyl ClCONHSO₂CH₂CH₃ 401 i-propyl H 3-chloro-2-thienyl Cl(isoxazol-3-ylamino)carbonyl 402 i-propyl H 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 403 i-propyl H phenylCl CONHCONHCH₃ 404 i-propyl H phenyl Cl CONHSO₂CF₃ 405 i-propyl H phenylCl CONHSO₂CH₃ 406 i-propyl H phenyl Cl CONHSO₂CH₂CH₃ 407 i-propyl Hphenyl Cl (isoxazol-3-ylamino)carbonyl 408 i-propyl H phenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 409 i-propyl Hcyclopentyl Cl CONHCONHCH₃ 410 i-propyl H cyclopentyl Cl CONHSO₂CF₃ 411i-propyl H cyclopentyl Cl CONHSO₂CH₃ 412 i-propyl H cyclopentyl ClCONHSO₂CH₂CH₃ 413 i-propyl H cyclopentyl Cl (isoxazol-3-ylamino)carbonyl414 i-propyl H cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 415 i-propyl H sec-butyl Cl CONHCONHCH₃ 416 i-propyl Hsec-butyl Cl CONHSO₂CF₃ 417 i-propyl H sec-butyl Cl CONHSO₂CH₃ 418i-propyl H sec-butyl Cl CONHSO₂CH₂CH₃ 419 i-propyl H sec-butyl Cl(isoxazol-3-ylamino)carbonyl 420 i-propyl H sec-butyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 421 i-butyl H2-chloro-6-fluorophenyl Cl CONHCONHCH₃ 422 i-butyl H2-chloro-6-fluorophenyl Cl CONHSO₂CF₃ 423 i-butyl H2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 424 i-butyl H2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 425 i-butyl H2-chloro-6-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 426 i-butyl H2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 427 i-butyl H 2,4,6-trifluorophenyl Cl CONHCONHCH₃ 428i-butyl H 2,4,6-trifluorophenyl Cl CONHSO₂CF₃ 429 i-butyl H2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 3.59* 430 i-butyl H2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 431 i-butyl H2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl 432 i-butyl H2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 433 i-butyl H 2-chloro-4-fluorophenyl Cl CONHCONHCH₃434 i-butyl H 2-chloro-4-fluorophenyl Cl CONHSO₂CF₃ 435 i-butyl H2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 3.82* 436 i-butyl H2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃ 437 i-butyl H2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 438 i-butyl H2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 439 i-butyl H 2-chlorophenyl Cl CONHCONHCH₃ 440i-butyl H 2-chlorophenyl Cl CONHSO₂CF₃ 441 i-butyl H 2-chlorophenyl ClCONHSO₂CH₃ 3.78* 442 i-butyl H 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 443i-butyl H 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl 444 i-butyl H2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 445i-butyl H 5-Cl-pyrimidin-4-yl Cl CONHCONHCH₃ 446 i-butyl H5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃ 447 i-butyl H 5-Cl-pyrimidin-4-yl ClCONHSO₂CH₃ 448 i-butyl H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 449i-butyl H 5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl 450i-butyl H 5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 451 i-butyl H 2-chloro-4,6- Cl CONHCONHCH₃difluorophenyl 452 i-butyl H 2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl453 i-butyl H 2-chloro-4,6- Cl CONHSO₂CH₃ difluorophenyl 454 i-butyl H2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 455 i-butyl H2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 456 i-butylH 2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 457 i-butyl H 2,4-dichlorophenyl Cl CONHCONHCH₃ 458i-butyl H 2,4-dichlorophenyl Cl CONHSO₂CF₃ 459 i-butyl H2,4-dichlorophenyl Cl CONHSO₂CH₃ 4.26* 460 i-butyl H 2,4-dichlorophenylCl CONHSO₂CH₂CH₃ 461 i-butyl H 2,4-dichlorophenyl Cl(isoxazol-3-ylamino)carbonyl 462 i-butyl H 2,4-dichlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 463 i-butyl H4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 464 i-butyl H 4-chloro-2,6-Cl CONHSO₂CF₃ difluorophenyl 465 i-butyl H 4-chloro-2,6- Cl CONHSO₂CH₃3.97* difluorophenyl 466 i-butyl H 4-chloro-2,6- Cl CONHSO₂CH₂CH₃difluorophenyl 467 i-butyl H 4-chloro-2,6- Cl(isoxazol-3-ylamino)carbonyl difluorophenyl 468 i-butyl H 4-chloro-2,6-Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 469i-butyl H 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl 470 i-butyl H2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl 471 i-butyl H 2,6-difluoro-4-Cl CONHSO₂CH₃ methylphenyl 472 i-butyl H 2,6-difluoro-4- ClCONHSO₂CH₂CH₃ methylphenyl 473 i-butyl H 2,6-difluoro-4- Cl(isoxazol-3-ylamino)carbonyl methylphenyl 474 i-butyl H 2,6-difluoro-4-Cl [(4-methyl-4H-1,2,4-triazol-3- methylphenyl yl)amino]carbonyl 475i-butyl H 2-chloro-5-fluorophenyl Cl CONHCONHCH₃ 476 i-butyl H2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 477 i-butyl H2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 478 i-butyl H2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 479 i-butyl H2-chloro-5-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 480 i-butyl H2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 481 i-butyl H 3-chloro-2-thienyl Cl CONHCONHCH₃ 482i-butyl H 3-chloro-2-thienyl Cl CONHSO₂CF₃ 483 i-butyl H3-chloro-2-thienyl Cl CONHSO₂CH₃ 484 i-butyl H 3-chloro-2-thienyl ClCONHSO₂CH₂CH₃ 485 i-butyl H 3-chloro-2-thienyl Cl(isoxazol-3-ylamino)carbonyl 486 i-butyl H 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 487 i-butyl H phenyl ClCONHCONHCH₃ 488 i-butyl H phenyl Cl CONHSO₂CF₃ 489 i-butyl H phenyl ClCONHSO₂CH₃ 490 i-butyl H phenyl Cl CONHSO₂CH₂CH₃ 491 i-butyl H phenyl Cl(isoxazol-3-ylamino)carbonyl 492 i-butyl H phenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 493 i-butyl Hcyclopentyl Cl CONHCONHCH₃ 494 i-butyl H cyclopentyl Cl CONHSO₂CF₃ 495i-butyl H cyclopentyl Cl CONHSO₂CH₃ 496 i-butyl H cyclopentyl ClCONHSO₂CH₂CH₃ 497 i-butyl H cyclopentyl Cl (isoxazol-3-ylamino)carbonyl498 i-butyl H cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 499 i-butyl H sec-butyl Cl CONHCONHCH₃ 500 i-butyl Hsec-butyl Cl CONHSO₂CF₃ 501 i-butyl H sec-butyl Cl CONHSO₂CH₃ 502i-butyl H sec-butyl Cl CONHSO₂CH₂CH₃ 503 i-butyl H sec-butyl Cl(isoxazol-3-ylamino)carbonyl 504 i-butyl H sec-butyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 505 CH₂—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHCONHCH₃ 506 CH₂—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHSO₂CF₃ 507 CH₂—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 4.04* 508 CH₂—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 509 CH₂—C(CH₃)₃ H2-chloro-6-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 510 CH₂—C(CH₃)₃H 2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 511 CH₂—C(CH₃)₃ H 2,4,6-trifluorophenyl Cl CONHCONHCH₃512 CH₂—C(CH₃)₃ H 2,4,6-trifluorophenyl Cl CONHSO₂CF₃ 513 CH₂—C(CH₃)₃ H2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 3.9* 514 CH₂—C(CH₃)₃ H2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 515 CH₂—C(CH₃)₃ H2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl 516 CH₂—C(CH₃)₃ H2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 517 CH₂—C(CH₃)₃ H 2-chloro-4-fluorophenyl ClCONHCONHCH₃ 518 CH₂—C(CH₃)₃ H 2-chloro-4-fluorophenyl Cl CONHSO₂CF₃ 519CH₂—C(CH₃)₃ H 2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 4.19* 520CH₂—C(CH₃)₃ H 2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃ 521 CH₂—C(CH₃)₃ H2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 522 CH₂—C(CH₃)₃H 2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 523 CH₂—C(CH₃)₃ H 2-chlorophenyl Cl CONHCONHCH₃ 524CH₂—C(CH₃)₃ H 2-chlorophenyl Cl CONHSO₂CF₃ 525 CH₂—C(CH₃)₃ H2-chlorophenyl Cl CONHSO₂CH₃ 4.17* 526 CH₂—C(CH₃)₃ H 2-chlorophenyl ClCONHSO₂CH₂CH₃ 527 CH₂—C(CH₃)₃ H 2-chlorophenyl Cl(isoxazol-3-ylamino)carbonyl 528 CH₂—C(CH₃)₃ H 2-chlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 529 CH₂—C(CH₃)₃ H5-Cl-pyrimidin-4-yl Cl CONHCONHCH₃ 530 CH₂—C(CH₃)₃ H 5-Cl-pyrimidin-4-ylCl CONHSO₂CF₃ 531 CH₂—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃ 532CH₂—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 533 CH₂—C(CH₃)₃ H5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl 534 CH₂—C(CH₃)₃ H5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl535 CH₂—C(CH₃)₃ H 2-chloro-4,6- Cl CONHCONHCH₃ difluorophenyl 536CH₂—C(CH₃)₃ H 2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl 537 CH₂—C(CH₃)₃H 2-chloro-4,6- Cl CONHSO₂CH₃ difluorophenyl 538 CH₂—C(CH₃)₃ H2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 539 CH₂—C(CH₃)₃ H2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 540CH₂—C(CH₃)₃ H 2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3-difluorophenyl yl)amino]carbonyl 541 CH₂—C(CH₃)₃ H 2,4-dichlorophenyl ClCONHCONHCH₃ 542 CH₂—C(CH₃)₃ H 2,4-dichlorophenyl Cl CONHSO₂CF₃ 543CH₂—C(CH₃)₃ H 2,4-dichlorophenyl Cl CONHSO₂CH₃ 4.63* 544 CH₂—C(CH₃)₃ H2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 545 CH₂—C(CH₃)₃ H 2,4-dichlorophenylCl (isoxazol-3-ylamino)carbonyl 546 CH₂—C(CH₃)₃ H 2,4-dichlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 547 CH₂—C(CH₃)₃ H4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 548 CH₂—C(CH₃)₃ H4-chloro-2,6- Cl CONHSO₂CF₃ difluorophenyl 549 CH₂—C(CH₃)₃ H4-chloro-2,6- Cl CONHSO₂CH₃ 4.31* difluorophenyl 550 CH₂—C(CH₃)₃ H4-chloro-2,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 551 CH₂—C(CH₃)₃ H4-chloro-2,6- Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 552CH₂—C(CH₃)₃ H 4-chloro-2,6- Cl [(4-methyl-4H-1,2,4-triazol-3-difluorophenyl yl)amino]carbonyl 553 CH₂—C(CH₃)₃ H 2,6-difluoro-4- ClCONHCONHCH₃ methylphenyl 554 CH₂—C(CH₃)₃ H 2,6-difluoro-4- Cl CONHSO₂CF₃methylphenyl 555 CH₂—C(CH₃)₃ H 2,6-difluoro-4- Cl CONHSO₂CH₃methylphenyl 556 CH₂—C(CH₃)₃ H 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃methylphenyl 557 CH₂—C(CH₃)₃ H 2,6-difluoro-4- Cl(isoxazol-3-ylamino)carbonyl methylphenyl 558 CH₂—C(CH₃)₃ H2,6-difluoro-4- Cl [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl 559 CH₂—C(CH₃)₃ H 2-chloro-5-fluorophenyl ClCONHCONHCH₃ 560 CH₂—C(CH₃)₃ H 2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 561CH₂—C(CH₃)₃ H 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 562 CH₂—C(CH₃)₃ H2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 563 CH₂—C(CH₃)₃ H2-chloro-5-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 564 CH₂—C(CH₃)₃H 2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 565 CH₂—C(CH₃)₃ H 3-chloro-2-thienyl Cl CONHCONHCH₃566 CH₂—C(CH₃)₃ H 3-chloro-2-thienyl Cl CONHSO₂CF₃ 567 CH₂—C(CH₃)₃ H3-chloro-2-thienyl Cl CONHSO₂CH₃ 568 CH₂—C(CH₃)₃ H 3-chloro-2-thienyl ClCONHSO₂CH₂CH₃ 569 CH₂—C(CH₃)₃ H 3-chloro-2-thienyl Cl(isoxazol-3-ylamino)carbonyl 570 CH₂—C(CH₃)₃ H 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 571 CH₂—C(CH₃)₃ Hphenyl Cl CONHCONHCH₃ 572 CH₂—C(CH₃)₃ H phenyl Cl CONHSO₂CF₃ 573CH₂—C(CH₃)₃ H phenyl Cl CONHSO₂CH₃ 574 CH₂—C(CH₃)₃ H phenyl ClCONHSO₂CH₂CH₃ 575 CH₂—C(CH₃)₃ H phenyl Cl (isoxazol-3-ylamino)carbonyl576 CH₂—C(CH₃)₃ H phenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 577 CH₂—C(CH₃)₃ H cyclopentyl Cl CONHCONHCH₃ 578CH₂—C(CH₃)₃ H cyclopentyl Cl CONHSO₂CF₃ 579 CH₂—C(CH₃)₃ H cyclopentyl ClCONHSO₂CH₃ 580 CH₂—C(CH₃)₃ H cyclopentyl Cl CONHSO₂CH₂CH₃ 581CH₂—C(CH₃)₃ H cyclopentyl Cl (isoxazol-3-ylamino)carbonyl 582CH₂—C(CH₃)₃ H cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 583 CH₂—C(CH₃)₃ H sec-butyl Cl CONHCONHCH₃ 584CH₂—C(CH₃)₃ H sec-butyl Cl CONHSO₂CF₃ 585 CH₂—C(CH₃)₃ H sec-butyl ClCONHSO₂CH₃ 586 CH₂—C(CH₃)₃ H sec-butyl Cl CONHSO₂CH₂CH₃ 587 CH₂—C(CH₃)₃H sec-butyl Cl (isoxazol-3-ylamino)carbonyl 588 CH₂—C(CH₃)₃ H sec-butylCl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 589—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl Cl CONHCONHCH₃ 590—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl Cl CONHSO₂CF₃ 591—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 592—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 593—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 594 —CH₂—CH₂—CH₂—CH(CH₃)—2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 595 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl ClCONHCONHCH₃ 596 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl ClCONHSO₂CF₃ 597 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl Cl CONHSO₂CH₃598 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 599—CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl Cl(isoxazol-3-ylamino)carbonyl 600 —CH₂—CH₂—CH₂—CH(CH₃)—2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 601 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl ClCONHCONHCH₃ 602 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl ClCONHSO₂CF₃ 603 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl ClCONHSO₂CH₃ 604 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl ClCONHSO₂CH₂CH₃ 605 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 606 —CH₂—CH₂—CH₂—CH(CH₃)—2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 607 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl ClCONHCONHCH₃ 608 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl Cl CONHSO₂CF₃ 609—CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl Cl CONHSO₂CH₃ 610—CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 611—CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl 612—CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 613 —CH₂—CH₂—CH₂—CH(CH₃)— 5-Cl-pyrimidin-4-yl ClCONHCONHCH₃ 614 —CH₂—CH₂—CH₂—CH(CH₃)— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃615 —CH₂—CH₂—CH₂—CH(CH₃)— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃ 616—CH₂—CH₂—CH₂—CH(CH₃)— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 617—CH₂—CH₂—CH₂—CH(CH₃)— 5-Cl-pyrimidin-4-yl Cl(isoxazol-3-ylamino)carbonyl 618 —CH₂—CH₂—CH₂—CH(CH₃)—5-Cl-pyrimidin-4-yl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl619 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4,6- Cl CONHCONHCH₃ difluorophenyl620 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl 621—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4,6- Cl CONHSO₂CH₃ difluorophenyl 622—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 623—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyldifluorophenyl 624 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 625—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-dichlorophenyl Cl CONHCONHCH₃ 626—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-dichlorophenyl Cl CONHSO₂CF₃ 627—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-dichlorophenyl Cl CONHSO₂CH₃ 628—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 629—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-dichlorophenyl Cl (isoxazol-3-ylamino)carbonyl630 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4-dichlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 631—CH₂—CH₂—CH₂—CH(CH₃)— 4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 632—CH₂—CH₂—CH₂—CH(CH₃)— 4-chloro-2,6- Cl CONHSO₂CF₃ difluorophenyl 633—CH₂—CH₂—CH₂—CH(CH₃)— 4-chloro-2,6- Cl CONHSO₂CH₃ difluorophenyl 634—CH₂—CH₂—CH₂—CH(CH₃)— 4-chloro-2,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 635—CH₂—CH₂—CH₂—CH(CH₃)— 4-chloro-2,6- Cl (isoxazol-3-ylamino)carbonyldifluorophenyl 636 —CH₂—CH₂—CH₂—CH(CH₃)— 4-chloro-2,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 637—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl 638—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl 639—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluoro-4- Cl CONHSO₂CH₃ methylphenyl 640—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃ methylphenyl 641—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluoro-4- Cl (isoxazol-3-ylamino)carbonylmethylphenyl 642 —CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluoro-4- Cl[(4-methyl-4H-1,2,4-triazol-3- methylphenyl yl)amino]carbonyl 643—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-5-fluorophenyl Cl CONHCONHCH₃ 644—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 645—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 646—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 647—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-5-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 648 —CH₂—CH₂—CH₂—CH(CH₃)—2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 649 —CH₂—CH₂—CH₂—CH(CH₃)— 3-chloro-2-thienyl ClCONHCONHCH₃ 650 —CH₂—CH₂—CH₂—CH(CH₃)— 3-chloro-2-thienyl Cl CONHSO₂CF₃651 —CH₂—CH₂—CH₂—CH(CH₃)— 3-chloro-2-thienyl Cl CONHSO₂CH₃ 652—CH₂—CH₂—CH₂—CH(CH₃)— 3-chloro-2-thienyl Cl CONHSO₂CH₂CH₃ 653—CH₂—CH₂—CH₂—CH(CH₃)— 3-chloro-2-thienyl Cl (isoxazol-3-ylamino)carbonyl654 —CH₂—CH₂—CH₂—CH(CH₃)— 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 655—CH₂—CH₂—CH₂—CH(CH₃)— phenyl Cl CONHCONHCH₃ 656 —CH₂—CH₂—CH₂—CH(CH₃)—phenyl Cl CONHSO₂CF₃ 657 —CH₂—CH₂—CH₂—CH(CH₃)— phenyl Cl CONHSO₂CH₃ 658—CH₂—CH₂—CH₂—CH(CH₃)— phenyl Cl CONHSO₂CH₂CH₃ 659 —CH₂—CH₂—CH₂—CH(CH₃)—phenyl Cl (isoxazol-3-ylamino)carbonyl 660 —CH₂—CH₂—CH₂—CH(CH₃)— phenylCl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 661—CH₂—CH₂—CH₂—CH(CH₃)— cyclopentyl Cl CONHCONHCH₃ 662—CH₂—CH₂—CH₂—CH(CH₃)— cyclopentyl Cl CONHSO₂CF₃ 663—CH₂—CH₂—CH₂—CH(CH₃)— cyclopentyl Cl CONHSO₂CH₃ 664—CH₂—CH₂—CH₂—CH(CH₃)— cyclopentyl Cl CONHSO₂CH₂CH₃ 665—CH₂—CH₂—CH₂—CH(CH₃)— cyclopentyl Cl (isoxazol-3-ylamino)carbonyl 666—CH₂—CH₂—CH₂—CH(CH₃)— cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 667 —CH₂—CH₂—CH₂—CH(CH₃)— sec-butyl Cl CONHCONHCH₃ 668—CH₂—CH₂—CH₂—CH(CH₃)— sec-butyl Cl CONHSO₂CF₃ 669 —CH₂—CH₂—CH₂—CH(CH₃)—sec-butyl Cl CONHSO₂CH₃ 670 —CH₂—CH₂—CH₂—CH(CH₃)— sec-butyl ClCONHSO₂CH₂CH₃ 671 —CH₂—CH₂—CH₂—CH(CH₃)— sec-butyl Cl(isoxazol-3-ylamino)carbonyl 672 —CH₂—CH₂—CH₂—CH(CH₃)— sec-butyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 673 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-6-fluorophenyl Cl CONHCONHCH₃ 674 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-6-fluorophenyl Cl CONHSO₂CF₃ 675 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-6-fluorophenyl Cl CONHSO₂CH₃ 676 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-6-fluorophenyl Cl CONHSO₂CH₂CH₃ 677 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-6-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 678—CH₂—CH₂—O—CH₂—CH₂— 2-chloro-6-fluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 679 —CH₂—CH₂—O—CH₂—CH₂—2,4,6-trifluorophenyl Cl CONHCONHCH₃ 680 —CH₂—CH₂—O—CH₂—CH₂—2,4,6-trifluorophenyl Cl CONHSO₂CF₃ 681 —CH₂—CH₂—O—CH₂—CH₂—2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 682 —CH₂—CH₂—O—CH₂—CH₂—2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 683 —CH₂—CH₂—O—CH₂—CH₂—2,4,6-trifluorophenyl Cl (isoxazol-3-ylamino)carbonyl 684—CH₂—CH₂—O—CH₂—CH₂— 2,4,6-trifluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 685 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4-fluorophenyl Cl CONHCONHCH₃ 686 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4-fluorophenyl Cl CONHSO₂CF₃ 687 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4-fluorophenyl Cl CONHSO₂CH₃ 688 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4-fluorophenyl Cl CONHSO₂CH₂CH₃ 689 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4-fluorophenyl Cl (isoxazol-3-ylamino)carbonyl 690—CH₂—CH₂—O—CH₂—CH₂— 2-chloro-4-fluorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 691 —CH₂—CH₂—O—CH₂—CH₂—2-chlorophenyl Cl CONHCONHCH₃ 692 —CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl ClCONHSO₂CF₃ 693 —CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl Cl CONHSO₂CH₃ 694—CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 695—CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl 696—CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 697 —CH₂—CH₂—O—CH₂—CH₂— 5-Cl-pyrimidin-4-yl ClCONHCONHCH₃ 698 —CH₂—CH₂—O—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃699 —CH₂—CH₂—O—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃ 700—CH₂—CH₂—O—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 701—CH₂—CH₂—O—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl702 —CH₂—CH₂—O—CH₂—CH₂— 5-Cl-pyrimidin-4-yl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 703 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4,6- Cl CONHCONHCH₃ difluorophenyl 704 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl 705 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4,6- Cl CONHSO₂CH₃ difluorophenyl 706 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 707 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyl difluorophenyl 708—CH₂—CH₂—O—CH₂—CH₂— 2-chloro-4,6- Cl [(4-methyl-4H-1,2,4-triazol-3-difluorophenyl yl)amino]carbonyl 709 —CH₂—CH₂—O—CH₂—CH₂—2,4-dichlorophenyl Cl CONHCONHCH₃ 710 —CH₂—CH₂—O—CH₂—CH₂—2,4-dichlorophenyl Cl CONHSO₂CF₃ 711 —CH₂—CH₂—O—CH₂—CH₂—2,4-dichlorophenyl Cl CONHSO₂CH₃ 712 —CH₂—CH₂—O—CH₂—CH₂—2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 713 —CH₂—CH₂—O—CH₂—CH₂—2,4-dichlorophenyl Cl (isoxazol-3-ylamino)carbonyl 714—CH₂—CH₂—O—CH₂—CH₂— 2,4-dichlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 715 —CH₂—CH₂—O—CH₂—CH₂— 4-chloro-2,6- Cl CONHCONHCH₃difluorophenyl 716 —CH₂—CH₂—O—CH₂—CH₂— 4-chloro-2,6- Cl CONHSO₂CF₃difluorophenyl 717 —CH₂—CH₂—O—CH₂—CH₂— 4-chloro-2,6- Cl CONHSO₂CH₃difluorophenyl 718 —CH₂—CH₂—O—CH₂—CH₂— 4-chloro-2,6- Cl CONHSO₂CH₂CH₃difluorophenyl 719 —CH₂—CH₂—O—CH₂—CH₂— 4-chloro-2,6- Cl(isoxazol-3-ylamino)carbonyl difluorophenyl 720 —CH₂—CH₂—O—CH₂—CH₂—4-chloro-2,6- Cl [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 721 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluoro-4- Cl CONHCONHCH₃methylphenyl 722 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluoro-4- Cl CONHSO₂CF₃methylphenyl 723 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluoro-4- Cl CONHSO₂CH₃methylphenyl 724 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃methylphenyl 725 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluoro-4- Cl(isoxazol-3-ylamino)carbonyl methylphenyl 726 —CH₂—CH₂—O—CH₂—CH₂—2,6-difluoro-4- Cl [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl 727 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-5-fluorophenyl ClCONHCONHCH₃ 728 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-5-fluorophenyl ClCONHSO₂CF₃ 729 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃730 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 731—CH₂—CH₂—O—CH₂—CH₂— 2-chloro-5-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 732 —CH₂—CH₂—O—CH₂—CH₂—2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 733 —CH₂—CH₂—O—CH₂—CH₂— 3-chloro-2-thienyl ClCONHCONHCH₃ 734 —CH₂—CH₂—O—CH₂—CH₂— 3-chloro-2-thienyl Cl CONHSO₂CF₃ 735—CH₂—CH₂—O—CH₂—CH₂— 3-chloro-2-thienyl Cl CONHSO₂CH₃ 736—CH₂—CH₂—O—CH₂—CH₂— 3-chloro-2-thienyl Cl CONHSO₂CH₂CH₃ 737—CH₂—CH₂—O—CH₂—CH₂— 3-chloro-2-thienyl Cl (isoxazol-3-ylamino)carbonyl738 —CH₂—CH₂—O—CH₂—CH₂— 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 739 —CH₂—CH₂—O—CH₂—CH₂—phenyl Cl CONHCONHCH₃ 740 —CH₂—CH₂—O—CH₂—CH₂— phenyl Cl CONHSO₂CF₃ 741—CH₂—CH₂—O—CH₂—CH₂— phenyl Cl CONHSO₂CH₃ 742 —CH₂—CH₂—O—CH₂—CH₂— phenylCl CONHSO₂CH₂CH₃ 743 —CH₂—CH₂—O—CH₂—CH₂— phenyl Cl(isoxazol-3-ylamino)carbonyl 744 —CH₂—CH₂—O—CH₂—CH₂— phenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 745 —CH₂—CH₂—O—CH₂—CH₂—cyclopentyl Cl CONHCONHCH₃ 746 —CH₂—CH₂—O—CH₂—CH₂— cyclopentyl ClCONHSO₂CF₃ 747 —CH₂—CH₂—O—CH₂—CH₂— cyclopentyl Cl CONHSO₂CH₃ 748—CH₂—CH₂—O—CH₂—CH₂— cyclopentyl Cl CONHSO₂CH₂CH₃ 749 —CH₂—CH₂—O—CH₂—CH₂—cyclopentyl Cl (isoxazol-3-ylamino)carbonyl 750 —CH₂—CH₂—O—CH₂—CH₂—cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 751—CH₂—CH₂—O—CH₂—CH₂— sec-butyl Cl CONHCONHCH₃ 752 —CH₂—CH₂—O—CH₂—CH₂—sec-butyl Cl CONHSO₂CF₃ 753 —CH₂—CH₂—O—CH₂—CH₂— sec-butyl Cl CONHSO₂CH₃754 —CH₂—CH₂—O—CH₂—CH₂— sec-butyl Cl CONHSO₂CH₂CH₃ 755—CH₂—CH₂—O—CH₂—CH₂— sec-butyl Cl (isoxazol-3-ylamino)carbonyl 756—CH₂—CH₂—O—CH₂—CH₂— sec-butyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 757 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-6-fluorophenyl ClCONHCONHCH₃ 758 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-6-fluorophenyl ClCONHSO₂CF₃ 759 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-6-fluorophenyl ClCONHSO₂CH₃ 760 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-6-fluorophenyl ClCONHSO₂CH₂CH₃ 761 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-6-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 762 —CH₂—CH₂—CH₂—CH₂—NH—2-chloro-6-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 763 —CH₂—CH₂—CH₂—CH₂—NH— 2,4,6-trifluorophenyl ClCONHCONHCH₃ 764 —CH₂—CH₂—CH₂—CH₂—NH— 2,4,6-trifluorophenyl Cl CONHSO₂CF₃765 —CH₂—CH₂—CH₂—CH₂—NH— 2,4,6-trifluorophenyl Cl CONHSO₂CH₃ 766—CH₂—CH₂—CH₂—CH₂—NH— 2,4,6-trifluorophenyl Cl CONHSO₂CH₂CH₃ 767—CH₂—CH₂—CH₂—CH₂—NH— 2,4,6-trifluorophenyl Cl(isoxazol-3-ylamino)carbonyl 768 —CH₂—CH₂—CH₂—CH₂—NH—2,4,6-trifluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 769 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4-fluorophenyl ClCONHCONHCH₃ 770 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4-fluorophenyl ClCONHSO₂CF₃ 771 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4-fluorophenyl ClCONHSO₂CH₃ 772 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4-fluorophenyl ClCONHSO₂CH₂CH₃ 773 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 774 —CH₂—CH₂—CH₂—CH₂—NH—2-chloro-4-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 775 —CH₂—CH₂—CH₂—CH₂—NH— 2-chlorophenyl Cl CONHCONHCH₃776 —CH₂—CH₂—CH₂—CH₂—NH— 2-chlorophenyl Cl CONHSO₂CF₃ 777—CH₂—CH₂—CH₂—CH₂—NH— 2-chlorophenyl Cl CONHSO₂CH₃ 778—CH₂—CH₂—CH₂—CH₂—NH— 2-chlorophenyl Cl CONHSO₂CH₂CH₃ 779—CH₂—CH₂—CH₂—CH₂—NH— 2-chlorophenyl Cl (isoxazol-3-ylamino)carbonyl 780—CH₂—CH₂—CH₂—CH₂—NH— 2-chlorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 781 —CH₂—CH₂—CH₂—CH₂—NH— 5-Cl-pyrimidin-4-yl ClCONHCONHCH₃ 782 —CH₂—CH₂—CH₂—CH₂—NH— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CF₃783 —CH₂—CH₂—CH₂—CH₂—NH— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₃ 784—CH₂—CH₂—CH₂—CH₂—NH— 5-Cl-pyrimidin-4-yl Cl CONHSO₂CH₂CH₃ 785—CH₂—CH₂—CH₂—CH₂—NH— 5-Cl-pyrimidin-4-yl Cl (isoxazol-3-ylamino)carbonyl786 —CH₂—CH₂—CH₂—CH₂—NH— 5-Cl-pyrimidin-4-yl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 787—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4,6- Cl CONHCONHCH₃ difluorophenyl 788—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4,6- Cl CONHSO₂CF₃ difluorophenyl 789—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4,6- Cl CONHSO₂CH₃ difluorophenyl 790—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 791—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4,6- Cl (isoxazol-3-ylamino)carbonyldifluorophenyl 792 —CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-4,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 793—CH₂—CH₂—CH₂—CH₂—NH— 2,4-dichlorophenyl Cl CONHCONHCH₃ 794—CH₂—CH₂—CH₂—CH₂—NH— 2,4-dichlorophenyl Cl CONHSO₂CF₃ 795—CH₂—CH₂—CH₂—CH₂—NH— 2,4-dichlorophenyl Cl CONHSO₂CH₃ 796—CH₂—CH₂—CH₂—CH₂—NH— 2,4-dichlorophenyl Cl CONHSO₂CH₂CH₃ 797—CH₂—CH₂—CH₂—CH₂—NH— 2,4-dichlorophenyl Cl (isoxazol-3-ylamino)carbonyl798 —CH₂—CH₂—CH₂—CH₂—NH— 2,4-dichlorophenyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 799—CH₂—CH₂—CH₂—CH₂—NH— 4-chloro-2,6- Cl CONHCONHCH₃ difluorophenyl 800—CH₂—CH₂—CH₂—CH₂—NH— 4-chloro-2,6- Cl CONHSO₂CF₃ difluorophenyl 801—CH₂—CH₂—CH₂—CH₂—NH— 4-chloro-2,6- Cl CONHSO₂CH₃ difluorophenyl 802—CH₂—CH₂—CH₂—CH₂—NH— 4-chloro-2,6- Cl CONHSO₂CH₂CH₃ difluorophenyl 803—CH₂—CH₂—CH₂—CH₂—NH— 4-chloro-2,6- Cl (isoxazol-3-ylamino)carbonyldifluorophenyl 804 —CH₂—CH₂—CH₂—CH₂—NH— 4-chloro-2,6- Cl[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 805—CH₂—CH₂—CH₂—CH₂—NH— 2,6-difluoro-4- Cl CONHCONHCH₃ methylphenyl 806—CH₂—CH₂—CH₂—CH₂—NH— 2,6-difluoro-4- Cl CONHSO₂CF₃ methylphenyl 807—CH₂—CH₂—CH₂—CH₂—NH— 2,6-difluoro-4- Cl CONHSO₂CH₃ methylphenyl 808—CH₂—CH₂—CH₂—CH₂—NH— 2,6-difluoro-4- Cl CONHSO₂CH₂CH₃ methylphenyl 809—CH₂—CH₂—CH₂—CH₂—NH— 2,6-difluoro-4- Cl (isoxazol-3-ylamino)carbonylmethylphenyl 810 —CH₂—CH₂—CH₂—CH₂—NH— 2,6-difluoro-4- Cl[(4-methyl-4H-1,2,4-triazol-3- methylphenyl yl)amino]carbonyl 811—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-5-fluorophenyl Cl CONHCONHCH₃ 812—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-5-fluorophenyl Cl CONHSO₂CF₃ 813—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-5-fluorophenyl Cl CONHSO₂CH₃ 814—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-5-fluorophenyl Cl CONHSO₂CH₂CH₃ 815—CH₂—CH₂—CH₂—CH₂—NH— 2-chloro-5-fluorophenyl Cl(isoxazol-3-ylamino)carbonyl 816 —CH₂—CH₂—CH₂—CH₂—NH—2-chloro-5-fluorophenyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 817 —CH₂—CH₂—CH₂—CH₂—NH— 3-chloro-2-thienyl ClCONHCONHCH₃ 818 —CH₂—CH₂—CH₂—CH₂—NH— 3-chloro-2-thienyl Cl CONHSO₂CF₃819 —CH₂—CH₂—CH₂—CH₂—NH— 3-chloro-2-thienyl Cl CONHSO₂CH₃ 820—CH₂—CH₂—CH₂—CH₂—NH— 3-chloro-2-thienyl Cl CONHSO₂CH₂CH₃ 821—CH₂—CH₂—CH₂—CH₂—NH— 3-chloro-2-thienyl Cl (isoxazol-3-ylamino)carbonyl822 —CH₂—CH₂—CH₂—CH₂—NH— 3-chloro-2-thienyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 823—CH₂—CH₂—CH₂—CH₂—NH— phenyl Cl CONHCONHCH₃ 824 —CH₂—CH₂—CH₂—CH₂—NH—phenyl Cl CONHSO₂CF₃ 825 —CH₂—CH₂—CH₂—CH₂—NH— phenyl Cl CONHSO₂CH₃ 826—CH₂—CH₂—CH₂—CH₂—NH— phenyl Cl CONHSO₂CH₂CH₃ 827 —CH₂—CH₂—CH₂—CH₂—NH—phenyl Cl (isoxazol-3-ylamino)carbonyl 828 —CH₂—CH₂—CH₂—CH₂—NH— phenylCl [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 829—CH₂—CH₂—CH₂—CH₂—NH— cyclopentyl Cl CONHCONHCH₃ 830 —CH₂—CH₂—CH₂—CH₂—NH—cyclopentyl Cl CONHSO₂CF₃ 831 —CH₂—CH₂—CH₂—CH₂—NH— cyclopentyl ClCONHSO₂CH₃ 832 —CH₂—CH₂—CH₂—CH₂—NH— cyclopentyl Cl CONHSO₂CH₂CH₃ 833—CH₂—CH₂—CH₂—CH₂—NH— cyclopentyl Cl (isoxazol-3-ylamino)carbonyl 834—CH₂—CH₂—CH₂—CH₂—NH— cyclopentyl Cl [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 835 —CH₂—CH₂—CH₂—CH₂—NH— sec-butyl Cl CONHCONHCH₃ 836—CH₂—CH₂—CH₂—CH₂—NH— sec-butyl Cl CONHSO₂CF₃ 837 —CH₂—CH₂—CH₂—CH₂—NH—sec-butyl Cl CONHSO₂CH₃ 838 —CH₂—CH₂—CH₂—CH₂—NH— sec-butyl ClCONHSO₂CH₂CH₃ 839 —CH₂—CH₂—CH₂—CH₂—NH— sec-butyl Cl(isoxazol-3-ylamino)carbonyl 840 —CH₂—CH₂—CH₂—CH₂—NH— sec-butyl Cl[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 841—CH₂—CH₂—CH₂—CH₂—NH— 2-methyl-cyclopentyl Cl CONHSO₂CH₃ 842CH(CH₃)—C(CH₃)₃ H 2-chloro-6-fluorophenyl CH₃ CONHCONHCH₃ 843CH(CH₃)—C(CH₃)₃ H 2-chloro-6-fluorophenyl CH₃ CONHSO₂CF₃ 844CH(CH₃)—C(CH₃)₃ H 2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₃ 845CH(CH₃)—C(CH₃)₃ H 2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 846CH(CH₃)—C(CH₃)₃ H 2-chloro-6-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 847 CH(CH₃)—C(CH₃)₃ H2-chloro-6-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 848 CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl CH₃CONHCONHCH₃ 849 CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl CH₃ CONHSO₂CF₃850 CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl CH₃ CONHSO₂CH₃ 851CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl CH₃ CONHSO₂CH₂CH₃ 852CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl CH₃ (isoxazol-3-ylamino)carbonyl853 CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 854 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl CH₃ CONHCONHCH₃ 855 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl CH₃ CONHSO₂CF₃ 856 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl CH₃ CONHSO₂CH₃ 857 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 858 CH(CH₃)—C(CH₃)₃ H2-chloro-4-fluorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 859CH(CH₃)—C(CH₃)₃ H 2-chloro-4-fluorophenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 860 CH(CH₃)—C(CH₃)₃ H2-chlorophenyl CH₃ CONHCONHCH₃ 861 CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl CH₃CONHSO₂CF₃ 862 CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl CH₃ CONHSO₂CH₃ 863CH(CH₃)—C(CH₃)₃ H 2-chlorophenyl CH₃ CONHSO₂CH₂CH₃ 864 CH(CH₃)—C(CH₃)₃ H2-chlorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 865 CH(CH₃)—C(CH₃)₃ H2-chlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 866CH(CH₃)—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl CH₃ CONHCONHCH₃ 867CH(CH₃)—C(CH₃)₃ H 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CF₃ 868 CH(CH₃)—C(CH₃)₃H 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₃ 869 CH(CH₃)—C(CH₃)₃ H5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₂CH₃ 870 CH(CH₃)—C(CH₃)₃ H5-Cl-pyrimidin-4-yl CH₃ (isoxazol-3-ylamino)carbonyl 871 CH(CH₃)—C(CH₃)₃H 5-Cl-pyrimidin-4-yl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 872 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- CH₃ CONHCONHCH₃difluorophenyl 873 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- CH₃ CONHSO₂CF₃difluorophenyl 874 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- CH₃ CONHSO₂CH₃difluorophenyl 875 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- CH₃ CONHSO₂CH₂CH₃difluorophenyl 876 CH(CH₃)—C(CH₃)₃ H 2-chloro-4,6- CH₃(isoxazol-3-ylamino)carbonyl difluorophenyl 877 CH(CH₃)—C(CH₃)₃ H2-chloro-4,6- CH₃ [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 878 CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl CH₃CONHCONHCH₃ 879 CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl CH₃ CONHSO₂CF₃ 880CH(CH₃)—C(CH₃)₃ H 2,4-dichlorophenyl CH₃ CONHSO₂CH₃ 881 CH(CH₃)—C(CH₃)₃H 2,4-dichlorophenyl CH₃ CONHSO₂CH₂CH₃ 882 CH(CH₃)—C(CH₃)₃ H2,4-dichlorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 883 CH(CH₃)—C(CH₃)₃H 2,4-dichlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 884 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- CH₃ CONHCONHCH₃difluorophenyl 885 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- CH₃ CONHSO₂CF₃difluorophenyl 886 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- CH₃ CONHSO₂CH₃difluorophenyl 887 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- CH₃ CONHSO₂CH₂CH₃difluorophenyl 888 CH(CH₃)—C(CH₃)₃ H 4-chloro-2,6- CH₃(isoxazol-3-ylamino)carbonyl difluorophenyl 889 CH(CH₃)—C(CH₃)₃ H4-chloro-2,6- CH₃ [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 890 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- CH₃ CONHCONHCH₃methylphenyl 891 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- CH₃ CONHSO₂CF₃methylphenyl 892 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- CH₃ CONHSO₂CH₃methylphenyl 893 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- CH₃ CONHSO₂CH₂CH₃methylphenyl 894 CH(CH₃)—C(CH₃)₃ H 2,6-difluoro-4- CH₃(isoxazol-3-ylamino)carbonyl methylphenyl 895 CH(CH₃)—C(CH₃)₃ H2,6-difluoro-4- CH₃ [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl 896 CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl CH₃CONHCONHCH₃ 897 CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl CH₃ CONHSO₂CF₃898 CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl CH₃ CONHSO₂CH₃ 899CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 900CH(CH₃)—C(CH₃)₃ H 2-chloro-5-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 901 CH(CH₃)—C(CH₃)₃ H2-chloro-5-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 902 CH(CH₃)—C(CH₃)₃ H 3-chloro-2-thienyl CH₃CONHCONHCH₃ 903 CH(CH₃)—C(CH₃)₃ H 3-chloro-2-thienyl CH₃ CONHSO₂CF₃ 904CH(CH₃)—C(CH₃)₃ H 3-chloro-2-thienyl CH₃ CONHSO₂CH₃ 905 CH(CH₃)—C(CH₃)₃H 3-chloro-2-thienyl CH₃ CONHSO₂CH₂CH₃ 906 CH(CH₃)—C(CH₃)₃ H3-chloro-2-thienyl CH₃ (isoxazol-3-ylamino)carbonyl 907 CH(CH₃)—C(CH₃)₃H 3-chloro-2-thienyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 908 CH(CH₃)—C(CH₃)₃ H phenyl CH₃ CONHCONHCH₃ 909CH(CH₃)—C(CH₃)₃ H phenyl CH₃ CONHSO₂CF₃ 910 CH(CH₃)—C(CH₃)₃ H phenyl CH₃CONHSO₂CH₃ 911 CH(CH₃)—C(CH₃)₃ H phenyl CH₃ CONHSO₂CH₂CH₃ 912CH(CH₃)—C(CH₃)₃ H phenyl CH₃ (isoxazol-3-ylamino)carbonyl 913CH(CH₃)—O(CH₃)₃ H phenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 914 CH(CH₃)—C(CH₃)₃ H cyclopentyl CH₃ CONHCONHCH₃ 915CH(CH₃)—C(CH₃)₃ H cyclopentyl CH₃ CONHSO₂CF₃ 916 CH(CH₃)—C(CH₃)₃ Hcyclopentyl CH₃ CONHSO₂CH₃ 917 CH(CH₃)—C(CH₃)₃ H cyclopentyl CH₃CONHSO₂CH₂CH₃ 918 CH(CH₃)—C(CH₃)₃ H cyclopentyl CH₃(isoxazol-3-ylamino)carbonyl 919 CH(CH₃)—C(CH₃)₃ H cyclopentyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 920 CH(CH₃)—C(CH₃)₃ Hsec-butyl CH₃ CONHCONHCH₃ 921 CH(CH₃)—C(CH₃)₃ H sec-butyl CH₃ CONHSO₂CF₃922 CH(CH₃)—C(CH₃)₃ H sec-butyl CH₃ CONHSO₂CH₃ 923 CH(CH₃)—C(CH₃)₃ Hsec-butyl CH₃ CONHSO₂CH₂CH₃ 924 CH(CH₃)—C(CH₃)₃ H sec-butyl CH₃(isoxazol-3-ylamino)carbonyl 925 CH(CH₃)—C(CH₃)₃ H sec-butyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 926 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl CH₃ CONHCONHCH₃ 927 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl CH₃ CONHSO₂CF₃ 928 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₃ 929 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 930 CH(CH₃)(CF₃) H2-chloro-6-fluorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 931CH(CH₃)(CF₃) H 2-chloro-6-fluorophenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 932 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl CH₃ CONHCONHCH₃ 933 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl CH₃ CONHSO₂CF₃ 934 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl CH₃ CONHSO₂CH₃ 935 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl CH₃ CONHSO₂CH₂CH₃ 936 CH(CH₃)(CF₃) H2,4,6-trifluorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 937 CH(CH₃)(CF₃)H 2,4,6-trifluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 938 CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl CH₃CONHCONHCH₃ 939 CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl CH₃ CONHSO₂CF₃940 CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl CH₃ CONHSO₂CH₃ 941CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 942CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl CH₃ (isoxazol-3-ylamino)carbonyl943 CH(CH₃)(CF₃) H 2-chloro-4-fluorophenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 944 CH(CH₃)(CF₃) H2-chlorophenyl CH₃ CONHCONHCH₃ 945 CH(CH₃)(CF₃) H 2-chlorophenyl CH₃CONHSO₂CF₃ 946 CH(CH₃)(CF₃) H 2-chlorophenyl CH₃ CONHSO₂CH₃ 947CH(CH₃)(CF₃) H 2-chlorophenyl CH₃ CONHSO₂CH₂CH₃ 948 CH(CH₃)(CF₃) H2-chlorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 949 CH(CH₃)(CF₃) H2-chlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 950CH(CH₃)(CF₃) H 5-Cl-pyrimidin-4-yl CH₃ CONHCONHCH₃ 951 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CF₃ 952 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₃ 953 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₂CH₃ 954 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl CH₃ (isoxazol-3-ylamino)carbonyl 955 CH(CH₃)(CF₃) H5-Cl-pyrimidin-4-yl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl956 CH(CH₃)(CF₃) H 2-chloro-4,6- CH₃ CONHCONHCH₃ difluorophenyl 957CH(CH₃)(CF₃) H 2-chloro-4,6- CH₃ CONHSO₂CF₃ difluorophenyl 958CH(CH₃)(CF₃) H 2-chloro-4,6- CH₃ CONHSO₂CH₃ difluorophenyl 959CH(CH₃)(CF₃) H 2-chloro-4,6- CH₃ CONHSO₂CH₂CH₃ difluorophenyl 960CH(CH₃)(CF₃) H 2-chloro-4,6- CH₃ (isoxazol-3-ylamino)carbonyldifluorophenyl 961 CH(CH₃)(CF₃) H 2-chloro-4,6- CH₃[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 962CH(CH₃)(CF₃) H 2,4-dichlorophenyl CH₃ CONHCONHCH₃ 963 CH(CH₃)(CF₃) H2,4-dichlorophenyl CH₃ CONHSO₂CF₃ 964 CH(CH₃)(CF₃) H 2,4-dichlorophenylCH₃ CONHSO₂CH₃ 965 CH(CH₃)(CF₃) H 2,4-dichlorophenyl CH₃ CONHSO₂CH₂CH₃966 CH(CH₃)(CF₃) H 2,4-dichlorophenyl CH₃ (isoxazol-3-ylamino)carbonyl967 CH(CH₃)(CF₃) H 2,4-dichlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 968 CH(CH₃)(CF₃) H 4-chloro-2,6- CH₃ CONHCONHCH₃difluorophenyl 969 CH(CH₃)(CF₃) H 4-chloro-2,6- CH₃ CONHSO₂CF₃difluorophenyl 970 CH(CH₃)(CF₃) H 4-chloro-2,6- CH₃ CONHSO₂CH₃difluorophenyl 971 CH(CH₃)(CF₃) H 4-chloro-2,6- CH₃ CONHSO₂CH₂CH₃difluorophenyl 972 CH(CH₃)(CF₃) H 4-chloro-2,6- CH₃(isoxazol-3-ylamino)carbonyl difluorophenyl 973 CH(CH₃)(CF₃) H4-chloro-2,6- CH₃ [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 974 CH(CH₃)(CF₃) H 2,6-difluoro-4- CH₃ CONHCONHCH₃methylphenyl 975 CH(CH₃)(CF₃) H 2,6-difluoro-4- CH₃ CONHSO₂CF₃methylphenyl 976 CH(CH₃)(CF₃) H 2,6-difluoro-4- CH₃ CONHSO₂CH₃methylphenyl 977 CH(CH₃)(CF₃) H 2,6-difluoro-4- CH₃ CONHSO₂CH₂CH₃methylphenyl 978 CH(CH₃)(CF₃) H 2,6-difluoro-4- CH₃(isoxazol-3-ylamino)carbonyl methylphenyl 979 CH(CH₃)(CF₃) H2,6-difluoro-4- CH₃ [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl 980 CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl CH₃CONHCONHCH₃ 981 CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl CH₃ CONHSO₂CF₃982 CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl CH₃ CONHSO₂CH₃ 983CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 984CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl CH₃ (isoxazol-3-ylamino)carbonyl985 CH(CH₃)(CF₃) H 2-chloro-5-fluorophenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 986 CH(CH₃)(CF₃) H3-chloro-2-thienyl CH₃ CONHCONHCH₃ 987 CH(CH₃)(CF₃) H 3-chloro-2-thienylCH₃ CONHSO₂CF₃ 988 CH(CH₃)(CF₃) H 3-chloro-2-thienyl CH₃ CONHSO₂CH₃ 989CH(CH₃)(CF₃) H 3-chloro-2-thienyl CH₃ CONHSO₂CH₂CH₃ 990 CH(CH₃)(CF₃) H3-chloro-2-thienyl CH₃ (isoxazol-3-ylamino)carbonyl 991 CH(CH₃)(CF₃) H3-chloro-2-thienyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl992 CH(CH₃)(CF₃) H phenyl CH₃ CONHCONHCH₃ 993 CH(CH₃)(CF₃) H phenyl CH₃CONHSO₂CF₃ 994 CH(CH₃)(CF₃) H phenyl CH₃ CONHSO₂CH₃ 995 CH(CH₃)(CF₃) Hphenyl CH₃ CONHSO₂CH₂CH₃ 996 CH(CH₃)(CF₃) H phenyl CH₃(isoxazol-3-ylamino)carbonyl 997 CH(CH₃)(CF₃) H phenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 998 CH(CH₃)(CF₃) Hcyclopentyl CH₃ CONHCONHCH₃ 999 CH(CH₃)(CF₃) H cyclopentyl CH₃CONHSO₂CF₃ 1000  CH(CH₃)(CF₃) H cyclopentyl CH₃ CONHSO₂CH₃ 1001 CH(CH₃)(CF₃) H cyclopentyl CH₃ CONHSO₂CH₂CH₃ 1002  CH(CH₃)(CF₃) Hcyclopentyl CH₃ (isoxazol-3-ylamino)carbonyl 1003  CH(CH₃)(CF₃) Hcyclopentyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1004 CH(CH₃)(CF₃) H sec-butyl CH₃ CONHCONHCH₃ 1005  CH(CH₃)(CF₃) H sec-butylCH₃ CONHSO₂CF₃ 1006  CH(CH₃)(CF₃) H sec-butyl CH₃ CONHSO₂CH₃ 1007 CH(CH₃)(CF₃) H sec-butyl CH₃ CONHSO₂CH₂CH₃ 1008  CH(CH₃)(CF₃) Hsec-butyl CH₃ (isoxazol-3-ylamino)carbonyl 1009  CH(CH₃)(CF₃) Hsec-butyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1010 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl CH₃ CONHCONHCH₃ 1011 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl CH₃ CONHSO₂CF₃ 1012 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₃ 1013 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 1014 CH(CH₃)—CH(CH₃)₂ H 2-chloro-6-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1015  CH(CH₃)—CH(CH₃)₂ H2-chloro-6-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1016  CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl CH₃CONHCONHCH₃ 1017  CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl CH₃CONHSO₂CF₃ 1018  CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl CH₃ CONHSO₂CH₃1019  CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl CH₃ CONHSO₂CH₂CH₃ 1020 CH(CH₃)—CH(CH₃)₂ H 2,4,6-trifluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1021  CH(CH₃)—CH(CH₃)₂ H2,4,6-trifluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1022  CH(CH₃)—CH(CH₃)₂ H 2-chloro-4-fluorophenyl CH₃CONHCONHCH₃ 1023  CH(CH₃)—CH(CH₃)₂ H 2-chloro-4-fluorophenyl CH₃CONHSO₂CF₃ 1024  CH(CH₃)—CH(CH₃)₂ H 2-chloro-4-fluorophenyl CH₃CONHSO₂CH₃ 1025  CH(CH₃)—CH(CH₃)₂ H 2-chloro-4-fluorophenyl CH₃CONHSO₂CH₂CH₃ 1026  CH(CH₃)—CH(CH₃)₂ H 2-chloro-4-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1027  CH(CH₃)—CH(CH₃)₂ H2-chloro-4-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1028  CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl CH₃CONHCONHCH₃ 1029  CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl CH₃ CONHSO₂CF₃ 1030 CH(CH₃)—CH(CH₃)₂ H 2-chlorophenyl CH₃ CONHSO₂CH₃ 1031  CH(CH₃)—CH(CH₃)₂H 2-chlorophenyl CH₃ CONHSO₂CH₂CH₃ 1032  CH(CH₃)—CH(CH₃)₂ H2-chlorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 1033  CH(CH₃)—CH(CH₃)₂ H2-chlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl1034  CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl CH₃ CONHCONHCH₃ 1035 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CF₃ 1036 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₃ 1037 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₂CH₃ 1038 CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl CH₃ (isoxazol-3-ylamino)carbonyl1039  CH(CH₃)—CH(CH₃)₂ H 5-Cl-pyrimidin-4-yl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1040  CH(CH₃)—CH(CH₃)₂H 2-chloro-4,6- CH₃ CONHCONHCH₃ difluorophenyl 1041  CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- CH₃ CONHSO₂CF₃ difluorophenyl 1042  CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- CH₃ CONHSO₂CH₃ difluorophenyl 1043  CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- CH₃ CONHSO₂CH₂CH₃ difluorophenyl 1044  CH(CH₃)—CH(CH₃)₂ H2-chloro-4,6- CH₃ (isoxazol-3-ylamino)carbonyl difluorophenyl 1045 CH(CH₃)—CH(CH₃)₂ H 2-chloro-4,6- CH₃ [(4-methyl-4H-1,2,4-triazol-3-difluorophenyl yl)amino]carbonyl 1046  CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl CH₃ CONHCONHCH₃ 1047  CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl CH₃ CONHSO₂CF₃ 1048  CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl CH₃ CONHSO₂CH₃ 1049  CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl CH₃ CONHSO₂CH₂CH₃ 1050  CH(CH₃)—CH(CH₃)₂ H2,4-dichlorophenyl CH₃ (isoxazol-3-ylamino)carbonyl 1051 CH(CH₃)—CH(CH₃)₂ H 2,4-dichlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1052  CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- CH₃ CONHCONHCH₃difluorophenyl 1053  CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- CH₃ CONHSO₂CF₃difluorophenyl 1054  CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- CH₃ CONHSO₂CH₃difluorophenyl 1055  CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- CH₃ CONHSO₂CH₂CH₃difluorophenyl 1056  CH(CH₃)—CH(CH₃)₂ H 4-chloro-2,6- CH₃(isoxazol-3-ylamino)carbonyl difluorophenyl 1057  CH(CH₃)—CH(CH₃)₂ H4-chloro-2,6- CH₃ [(4-methyl-4H-1,2,4-triazol-3- difluorophenylyl)amino]carbonyl 1058  CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- CH₃CONHCONHCH₃ methylphenyl 1059  CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- CH₃CONHSO₂CF₃ methylphenyl 1060  CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- CH₃CONHSO₂CH₃ methylphenyl 1061  CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- CH₃CONHSO₂CH₂CH₃ methylphenyl 1062  CH(CH₃)—CH(CH₃)₂ H 2,6-difluoro-4- CH₃(isoxazol-3-ylamino)carbonyl methylphenyl 1063  CH(CH₃)—CH(CH₃)₂ H2,6-difluoro-4- CH₃ [(4-methyl-4H-1,2,4-triazol-3- methylphenylyl)amino]carbonyl 1064  CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl CH₃CONHCONHCH₃ 1065  CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl CH₃CONHSO₂CF₃ 1066  CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl CH₃CONHSO₂CH₃ 1067  CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl CH₃CONHSO₂CH₂CH₃ 1068  CH(CH₃)—CH(CH₃)₂ H 2-chloro-5-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1069  CH(CH₃)—CH(CH₃)₂ H2-chloro-5-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1070  CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl CH₃CONHCONHCH₃ 1071  CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl CH₃ CONHSO₂CF₃1072  CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl CH₃ CONHSO₂CH₃ 1073 CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl CH₃ CONHSO₂CH₂CH₃ 1074 CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl CH₃ (isoxazol-3-ylamino)carbonyl1075  CH(CH₃)—CH(CH₃)₂ H 3-chloro-2-thienyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1076  CH(CH₃)—CH(CH₃)₂H phenyl CH₃ CONHCONHCH₃ 1077  CH(CH₃)—CH(CH₃)₂ H phenyl CH₃ CONHSO₂CF₃1078  CH(CH₃)—CH(CH₃)₂ H phenyl CH₃ CONHSO₂CH₃ 1079  CH(CH₃)—CH(CH₃)₂ Hphenyl CH₃ CONHSO₂CH₂CH₃ 1080  CH(CH₃)—CH(CH₃)₂ H phenyl CH₃(isoxazol-3-ylamino)carbonyl 1081  CH(CH₃)—CH(CH₃)₂ H phenyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1082  CH(CH₃)—CH(CH₃)₂H cyclopentyl CH₃ CONHCONHCH₃ 1083  CH(CH₃)—CH(CH₃)₂ H cyclopentyl CH₃CONHSO₂CF₃ 1084  CH(CH₃)—CH(CH₃)₂ H cyclopentyl CH₃ CONHSO₂CH₃ 1085 CH(CH₃)—CH(CH₃)₂ H cyclopentyl CH₃ CONHSO₂CH₂CH₃ 1086  CH(CH₃)—CH(CH₃)₂H cyclopentyl CH₃ (isoxazol-3-ylamino)carbonyl 1087  CH(CH₃)—CH(CH₃)₂ Hcyclopentyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1088 CH(CH₃)—CH(CH₃)₂ H sec-butyl CH₃ CONHCONHCH₃ 1089  CH(CH₃)—CH(CH₃)₂ Hsec-butyl CH₃ CONHSO₂CF₃ 1090  CH(CH₃)—CH(CH₃)₂ H sec-butyl CH₃CONHSO₂CH₃ 1091  CH(CH₃)—CH(CH₃)₂ H sec-butyl CH₃ CONHSO₂CH₂CH₃ 1092 CH(CH₃)—CH(CH₃)₂ H sec-butyl CH₃ (isoxazol-3-ylamino)carbonyl 1093 CH(CH₃)—CH(CH₃)₂ H sec-butyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1094  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-6-fluorophenyl CH₃ CONHCONHCH₃ 1095  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-6-fluorophenyl CH₃ CONHSO₂CF₃ 1096  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₃ 1097  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-6-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 1098 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1099  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-6-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1100  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenylCH₃ CONHCONHCH₃ 1101  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenylCH₃ CONHSO₂CF₃ 1102  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl CH₃CONHSO₂CH₃ 1103  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl CH₃CONHSO₂CH₂CH₃ 1104  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1105  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2,4,6-trifluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1106  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4-fluorophenyl CH₃ CONHCONHCH₃ 1107  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4-fluorophenyl CH₃ CONHSO₂CF₃ 1108  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4-fluorophenyl CH₃ CONHSO₂CH₃ 1109  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4-fluorophenyl CH₃ CONHSO₂CH₂CH₃ 1110 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1111  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1112  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl CH₃CONHCONHCH₃ 1113  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl CH₃CONHSO₂CF₃ 1114  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl CH₃ CONHSO₂CH₃1115  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl CH₃ CONHSO₂CH₂CH₃ 1116 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1117  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl1118  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl CH₃ CONHCONHCH₃1119  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CF₃ 1120 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₃ 1121 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl CH₃ CONHSO₂CH₂CH₃ 1122 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 5-Cl-pyrimidin-4-yl CH₃(isoxazol-3-ylamino)carbonyl 1123  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—5-Cl-pyrimidin-4-yl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl1124  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- CH₃ CONHCONHCH₃difluorophenyl 1125  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- CH₃CONHSO₂CF₃ difluorophenyl 1126  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6-CH₃ CONHSO₂CH₃ difluorophenyl 1127  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-4,6- CH₃ CONHSO₂CH₂CH₃ difluorophenyl 1128 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- CH₃ (isoxazol-3-ylamino)carbonyldifluorophenyl 1129  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4,6- CH₃[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 1130 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl CH₃ CONHCONHCH₃ 1131 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl CH₃ CONHSO₂CF₃ 1132 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl CH₃ CONHSO₂CH₃ 1133 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl CH₃ CONHSO₂CH₂CH₃ 1134 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-dichlorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1135  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2,4-dichlorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl1136  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- CH₃ CONHCONHCH₃difluorophenyl 1137  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- CH₃CONHSO₂CF₃ difluorophenyl 1138  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6-CH₃ CONHSO₂CH₃ difluorophenyl 1139  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—4-chloro-2,6- CH₃ CONHSO₂CH₂CH₃ difluorophenyl 1140 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- CH₃ (isoxazol-3-ylamino)carbonyldifluorophenyl 1141  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 4-chloro-2,6- CH₃[(4-methyl-4H-1,2,4-triazol-3- difluorophenyl yl)amino]carbonyl 1142 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- CH₃ CONHCONHCH₃ methylphenyl1143  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- CH₃ CONHSO₂CF₃methylphenyl 1144  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- CH₃CONHSO₂CH₃ methylphenyl 1145  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4-CH₃ CONHSO₂CH₂CH₃ methylphenyl 1146  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2,6-difluoro-4- CH₃ (isoxazol-3-ylamino)carbonyl methylphenyl 1147 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluoro-4- CH₃[(4-methyl-4H-1,2,4-triazol-3- methylphenyl yl)amino]carbonyl 1148 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl CH₃ CONHCONHCH₃ 1149 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl CH₃ CONHSO₂CF₃ 1150 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl CH₃ CONHSO₂CH₃ 1151 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl CH₃ CONHSO₂CH₂CH₃1152  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-5-fluorophenyl CH₃(isoxazol-3-ylamino)carbonyl 1153  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—2-chloro-5-fluorophenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1154  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl CH₃CONHCONHCH₃ 1155  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl CH₃CONHSO₂CF₃ 1156  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl CH₃CONHSO₂CH₃ 1157  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl CH₃CONHSO₂CH₂CH₃ 1158  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 3-chloro-2-thienyl CH₃(isoxazol-3-ylamino)carbonyl 1159  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—3-chloro-2-thienyl CH₃ [(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl1160  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl CH₃ CONHCONHCH₃ 1161 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl CH₃ CONHSO₂CF₃ 1162 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl CH₃ CONHSO₂CH₃ 1163 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl CH₃ CONHSO₂CH₂CH₃ 1164 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl CH₃ (isoxazol-3-ylamino)carbonyl 1165 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— phenyl CH₃ [(4-methyl-4H-1,2,4-triazol-3-yl)amino]carbonyl 1166  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl CH₃CONHCONHCH₃ 1167  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl CH₃ CONHSO₂CF₃1168  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl CH₃ CONHSO₂CH₃ 1169 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl CH₃ CONHSO₂CH₂CH₃ 1170 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl CH₃ (isoxazol-3-ylamino)carbonyl1171  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— cyclopentyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1172 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl CH₃ CONHCONHCH₃ 1173 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl CH₃ CONHSO₂CF₃ 1174 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl CH₃ CONHSO₂CH₃ 1175 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl CH₃ CONHSO₂CH₂CH₃ 1176 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl CH₃ (isoxazol-3-ylamino)carbonyl1177  —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— sec-butyl CH₃[(4-methyl-4H-1,2,4-triazol-3- yl)amino]carbonyl 1178  (R)CH(CH₃)—CH(CH₃)₂ H 4-fluoro-2- Cl CONHCONHCH₃ 4.42 methylphenyl 1179 CH(CH3)—CH(CH3)2 H 4-fluoro-2- Cl pyrimidin-2-ylaminocarbonyl 6.61methylphenyl 1180  CH(CH3)—CH(CH3)2 H 2,4-difluorophenyl Clmorpholin-4-ylaminocarbonyl 3.46 1181  CH(CH3)—C(CH3)3 H 2-chloro-4- Clmorpholin-4-ylaminocarbonyl 4.41 methylphenyl 1182  CH(CH3)—C(CH3)3 H2,4-difluorophenyl Cl morpholin-4-ylaminocarbonyl 3.76 1183 CH(CH3)—CH(CH3)2 H 3-Me-thien-2-yl Cl morpholin-4-ylaminocarbonyl 3.631184  CH(CH3)—CH(CH3)2 H 2-chloro-4-fluorophenyl Cl1-methylpyrazol-3-yl- 4.35 aminocarbonyl 1185  CH(CH3)—C(CH3)3 H2-chloro-4-fluorophenyl Cl 1-methylpyrazol-3-yl- 4.69 aminocarbonyl1186  CH(CH3)—CH(CH3)2 H 2-chloro-4-fluorophenyl Cl1-methylpyrazol-5-yl- 4.18 aminocarbonyl 1187  CH(CH3)—C(CH3)3 H2-chloro-4-fluorophenyl Cl 1-methylpyrazol-4-yl- 4.26 aminocarbonyl1188  CH(CH3)—CH(CH3)2 H 2-chloro-4-fluorophenyl Cl1-methyl-1,2,4-triazol-3-yl- 3.62 aminocarbonyl 1189  CH(CH3)—CH(CH3)2 H2-chloro-4-fluorophenyl Cl 1-methylpyrazol-4-yl- 3.95 aminocarbonyl1190  CH(CH3)—CH(CH3)2 H 2,4-difluorophenyl Cl CONHSO₂CH₃ 3.87 1191 CH(CH3)—C(CH3)3 H 2-chloro-4-fluorophenyl Cl 1-methyl-1,2,4-triazol-3-3.91 ylaminocarbonyl 1192  —CH2—CH2—CH(CH3)— 2-chloro-4-fluorophenyl Cl1-methyl-1,2,4-triazol-3- 3.89 CH2—CH2— ylaminocarbonyl 1193 —CH2—CH2—CH(CH3)— 2-chloro-4-fluorophenyl Cl 1-methylpyrazol-5- 4.47CH2—CH2— ylaminocarbonyl 1194  CH(CH3)—C(CH3)3 H 2-chloro-4- ClCONHSO₂CH₃ 4.76 methylphenyl 1195  —CH2—CH2—CH(CH3)—2-chloro-4-fluorophenyl Cl 1-methylpyrazol-3- 4.66 CH2—CH2—ylaminocarbonyl 1196  —CH2—CH2—CH(CH3)— 2-chloro-4-fluorophenyl Cl1-methylpyrazol-4- 4.31 CH2—CH2— ylaminocarbonyl 1197  —CH2—CH2—CH(CH3)—2-chloro-4-fluorophenyl Cl 1,2,4-triazol-5- 4.11 CH2—CH2—ylaminocarbonyl 1198  CH(CH3)—CH(CH3)2 H 2,6-dichloro-4- Cl CONHSO₂CH₃4.85 (trifluoromethoxy)- phenyl The logP values were determined inaccordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradientmethod, acetonitrile/0.1% aqueous phosphoric acid). **These logP valueswere determined in accordance with EEC Directive 79/831 Annex V.A8 byHPLC (gradient method, acetonitrile/0.1% aqueous formic acid).Preparation of the Starting Materials:

In an apparatus with Vigreux column, 198 g (1998 mmol) of methylcyanoacetate, 296 g (1998 mmol) of triethyl orthoformate and 440 g (4310mmol) of acetic anhydride were heated at reflux. Volatile componentswere distilled off until a head temperature of 120° C. had been reached.After cooling, the mixture was fractionated under reduced pressure. Thisgave 5 g of methyl (2E/Z)-2-cyano-3-ethoxyacrylate (fraction 1: 65-100°C., 0.2 mbar, 88% pure according to GCMS) and a further 209 g of methyl(2E/Z)-2-cyano-3-ethoxyacrylate (fraction 2: 105-108° C., 0.2 mbar, >99%pure according to GCMS).

100 g (645 mmol) of methyl (2E/Z)-2-cyano-3-ethoxyacrylate wereinitially charged in 481 ml of ethanol. 31 ml (645 mmol) of an 85%strength hydrazine hydrate solution were then added dropwise at roomtemperature with cooling (exothermal temperature!) over a period of 45minutes. The mixture was stirred at 75° C. for another 12 hours. The hotmixture was filtered and the organic phase was concentrated underreduced pressure. This gave 64 g of methyl5-amino-1H-pyrazole-4-carboxylate (log P=−0.07; HPLC content: 86%).

Methyl6-(2,4-dichlorophenyl)-5,7-dihydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate

5.5 g of dimethyl 2-(2,4-dichlorophenyl)malonate and 2.8 g of methyl3-aminopyrazole-4-carboxylate were mixed with 4 g of tri-n-butylamineand stirred at 185° C. for 3 h; the liberated methanol was distilled offduring this operation. The mixture was then cooled and excesstri-n-butylamine was removed under reduced pressure. The resultingproduct was reacted crude, without further purification.

log P*: 1.21

Methyl5,7-dichloro-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

10 g of methyl6-(2,4-dichlorophenyl)-5,7-dihydroxypyrazolo[1,5-a]pyrimidine-3-carboxylatewere dissolved in 43.3 g of phosphoryl chloride and stirred at 120° C.for 3-4 h, until the evolution of gas had ceased. 2.94 g of phosphoruspentachloride were then added, and the mixture was stirred at 120° C.for another 2-3 h. After subsequent cooling, the mixture wasconcentrated on a rotary evaporator and taken up in water anddichloromethane. The organic phase was separated off and dried withsodium sulphate, and the solvent was removed under reduced pressure. Theresidue was purified chromatographically (silica gel, cyclohexane/ethylacetate 9:1, 5:1, 3:1). This gave the title compound.

log P*: 3.86

Methyl5-chloro-6-(2,4-dichlorophenyl)-7-isopropylaminopyrazolo[1,5-a]pyrimidine-3-carboxylate

5 g of the dichloro compound obtained above were dissolved in 50 ml ofacetonitrile, and 0.831 g of isopropylamine were added. Withice-cooling, 2.651 g of potassium carbonate were added and the mixturewas stirred at room temperature for 15 h (monitored by TLC). The mixturewas then neutralized with 1 N hydrochloric acid and filtered off withsuction. Solid.

log P*: 4.07

5-Chloro-6-(2,4-dichlorophenyl)-7-isopropylaminopyrazolo[1,5-a]pyrimidine-3-carboxylicacid

5 g of methyl5-chloro-6-(2,4-dichlorophenyl)-7-isopropylaminopyrazolo[1,5-a]pyrimidine-3-carboxylatewere dissolved in 75 ml of 1,4-dioxane, and 75 ml of 2 N aqueouspotassium hydroxide solution were added. The mixture was stirred at roomtemperature for 15 h (monitored by TLC) and then introduced into 1 Nhydrochloric acid. The precipitated solid was filtered off with suction.

log P*: 3.30

The following intermediates were prepared analogously:

R¹ R² R³ log P CH(CH₃)—C(CH₃)₃ H 5-F-pyrimidin-4-yl 3.15CH(CH₃)—CH(CH₃)₂ H 2-Cl-6-F-phenyl 4.12 (CH₂—CH₂—CHCH₃—CH₂—CH₂)2-Cl-6-F-phenyl 4.61 CH(CH₃)—C(CH₃)₃ H 2-Cl-6-F-phenyl 4.51CH(CH₃)—C(CH₃)₃ H 2,4,6-trifluorophenyl 4.93 CH(CH₃)—CH(CH₃)₂ H2,4,6-trifluorophenyl 4.05 CH(CH₃)(CF₃) H 2,4,6-trifluorophenyl 3.53CH(CH₃)(CF₃) H 2-Cl-4-F-phenyl 3.75 CH(CH₃)—CH(CH₃)₂ H 2-Cl-4-F-phenyl4.31 CH(CH₃)—C(CH₃)₃ H 2-Cl-4-F-phenyl 4.68 CH(CH₃)—CH(CH₃)₂ H2-Cl-phenyl 4.21 CH(CH₃)—C(CH₃)₃ H 2-Cl-phenyl 4.61

Dimethyl 2-(3-methylthiophen-2-yl)malonate

Aluminium trichloride (163 g, 1.222 mol) was initially charged in 540 mlof dichloromethane, the mixture was cooled to 0° C. and 112 ml (150 g,1.222 mol) of methyl oxalyl chloride were added dropwise at thistemperature. The mixture was then stirred at this temperature foranother 10 min, also at 0° C., 3-methylthiophene was then addeddropwise, and after warming to room temperature, the reaction mixturewas stirred at this temperature overnight. The mixture was hydrolysed bypouring into 2 l of ice-water, and the organic phase was separated off,washed with sodium bicarbonate solution and dried over sodium sulphategiving, after removal of drying agent by filtration and concentrationusing a rotary evaporator, 119.5 g of methyl(3-methylthiophen-2-yl)oxoacetate. Yield: 57%. ¹H-NMR (DMSO): δ=8.09 (d,1H), 7.19 (d, 1H), 7.67 (dd, 1H), 3.90 (s, 3H), 2.49 (s, 3H).

112.5 ml (116 g, 2.312 mol) of hydrazine hydrate were added slowly to asolution of 90 g (0.489 mol) of methyl (3-methylthiophen-2-yl)oxoacetatein 260 ml of diethylene glycol, and the mixture was heated at reflux for30 min. After cooling to 30-40° C., 82 g (1.246 mol) of potassiumhydroxide were added a little at a time, which was associated with atemperature increase to 70-80° C. with simultaneous evolution ofnitrogen. The mixture was then slowly heated to reflux and stirred atthis temperature for a total of 5 h. After cooling to room temperature,the mixture was poured into 2 l of water, adjusted to pH=1 using 250 mlof semiconcentrated hydrochloric acid and extracted with ethyl acetate.Drying of the organic phase over magnesium sulphate, filtration andremoval of the solvent gave 50 g of (3-methylthiophen-2-yl)acetic acid.Yield: 66%. ¹H-NMR (DMSO): δ=7.25 (d, 1H), 6.84 (d, 2H), 3.67 (s, 2H),2.11 (s, 3H).

5 ml of concentrated sulphuric acid were added to a solution of 50 g(0.32 mol) of (3-methylthiophen-2-yl)acetic acid in 500 ml of methanol,and the mixture was heated at reflux for 8 h. The solvent was thenremoved using a rotary evaporator, and water and dichloromethane wereadded to the residue. Separation of the phases and re-extraction of theaqueous phase with dichloromethane gave, after drying of the organicphase over sodium sulphate, filtration and concentration using a rotaryevaporator, 42.5 g of methyl (3-methylthiophen-2-yl)acetate. Yield: 70%.¹H-NMR (DMSO): δ=7.30 (d, 1H), 6.87 (d, 1H), 3.82 (s, 2H), 3.65 (s, 3H),2.13 (s, 3H).

Under argon, 14.7 g of sodium hydride (60% in mineral oil) were added to311 ml (332 g, 3.685 mol) of dimethyl carbonate, and the mixture washeated to 80° C. A solution of 41 g (0.217 mol) of methyl(3-methylthiophen-2-yl)acetate in 50 ml of toluene was slowly addeddropwise at this temperature, and the mixture was stirred at refluxovernight. For work-up, the mixture was diluted with about 200 ml ofmethanol, poured into ice-water and acidified with dilute hydrochloricacid. Extraction with dichloromethane, drying of the organic phase oversodium sulphate, filtration and removal of the solvent gave 43.6 g ofdimethyl 2-(3-methylthiophen-2-yl)malonate. Yield: 88%. ¹H-NMR (DMSO):δ=7.42 (d, 1H), 6.89 (d, 1H), 5.27 (s, 1H), 3.69 (s, 6H), 2.15 (s, 3H).

Spectroscopic Data of the Analogously Prepared Intermediates:

Structure ¹H-NMR (DMSO)

δ = 8.30 (d, 1H), 7.36 (d, 1H), 3.92 (s, 3H)

δ = 7.54 (d, 1H), 7.02 (d, 1H), 3.78 (s, 2H)

δ = 7.57 (d, 1H), 7.04 (d, 1H), 3.90 (s, 2H), 3.66 (s, 3H)

δ = 7.71 (d, 1H), 7.08 (d, 1H), 5.25 (s, 1H), 3.73 (s, 6H)

δ = 7.42 (d, 1H), 7.00 (d, 1H), 3.66 (s, 2H), 3.63 (s, 3H)

δ = 7.49 (d, 1H), 7.05 (d, 1H), 4.98 (s, 1H), 3.70 (s, 6H)

USE EXAMPLES Example A Podosphaera Test (Apple)/Protective

Solvents: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of the apple mildew pathogen Podosphaera leucotricha.The plants are then placed in a greenhouse at about 23° C. and arelative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compounds according to the invention of the examplenumbers below showed, at an active compound concentration of 100 ppm, anefficacy of 70% or more.

9, 15, 33, 38, 39, 45, 117, 123, 171, 183, 189, 207, 261, 285, 357, 441,465, 519, 543, 549

Example B Venturia Test (Apple)/Protective

Solvents: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compounds according to the invention of the examplenumbers below showed, at an active compound concentration of 100 ppm, anefficacy of 70% or more.

3, 9, 14, 15, 21, 33, 38, 39, 45, 117, 123, 171, 177, 183, 189, 201,207, 213, 255, 261, 285, 345, 351, 357, 381, 435, 441, 459, 465, 507,513, 519, 525, 543, 549, 1178

Example C Botrytis Test (Bean)/Protective

Solvents: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, 2 small pieces of agar colonized by Botrytiscinerea are placed onto each leaf. The inoculated plants are placed in adark chamber at about 20° C. and 100% relative atmospheric humidity.

The size of the infected areas on the leaves is evaluated 2 days afterthe inoculation. 0% means an efficacy which corresponds to that of thecontrol, whereas an efficacy of 100% means that no infection isobserved.

In this test, the compounds according to the invention of the examplenumbers below showed, at an active compound concentration of 100 ppm, anefficacy of 70% or more.

3, 9, 14, 15, 21, 33, 38, 39, 45, 117, 123, 171, 177, 183, 189, 201,207, 213, 255, 261, 285, 345, 351, 357, 381, 435, 441, 459, 465, 507,513, 519, 525, 543, 549, 1178

Example D Sphaerotheca Test (Cucumber)/Protective

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young cucumber plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Sphaerotheca fuliginea. The plants are then placed in a greenhouse at70% relative atmospheric humidity and a temperature of 23° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compounds according to the invention of the formulaebelow show, at an active compound concentration of 500 ppm, an efficacyof 70% or more.

9, 14, 15, 33, 38, 123, 183, 351, 357, 429, 465

Example E Puccinia Test (Wheat)/Protective

Solvent: 50 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the compounds according to the invention below show, at anactive compound concentration of 1000 ppm, an efficacy of 70% or more.

3, 9, 15, 33, 45, 117, 123, 177, 201, 207, 255, 285, 345, 381, 435, 441,465, 507, 513, 549

Example F

Compounds of the present invention were tested for a possible cytotoxicor proliferation-inhibiting activity on the human tumour cell linesHeLa, SW620 and A375 (all from ATCC, American Type Culture Collection).To this end, the cells were plated in microtitre plates from Greiner(manufacturer No. 781092) at a cell density of 1000 cells/microtitreplate well and cultivated in cell culture medium at 37° C. under a 5%carbon dioxide atmosphere. Cell culture media and additives werepurchased from Invitrogen and the foetal calf serum from Biochrom. Thecell culture media for HeLa and A375 cells were used as stated by ATCC(HeLa: MEM, order No. 10370-047, with 1% sodium bicarbonate, 1%non-essential amino acids, 1% sodium pyruvate, 10% foetal calf serum,0.1% gentamycin; A375: DMEM, order No. 41965-039, 2% sodium bicarbonate,1% L-Glutamax, 10% foetal calf serum, 0.1% gentamycin). The culturemedium for the SW620 cells consisted of DMEM, order No. 41965-039, 1%non-essential amino acids, 10% foetal calf serum, 0.1% gentamycin.

24 hours after the cells had been plated in the microtitre plates,various concentrations of at most 100 μM down to a minimum concentrationof 5 nM of the test compounds were added to the cells. Stock solutionsof the test compounds (10 mM) were prepared in DMSO and stored at −20°C. For the cytotoxicity tests, the test compounds were diluted in theappropriate cell culture medium.

After a further 48 hours of incubation, the cells were washed withmedium and analysed with the aid of a two-colour fluorescencecytotoxicity/viability test (LIVE/DEAD Viability/Cytotoxicity ASSAY Kitfrom Molecular Probes, order No. L-3224), according to the instructionsof the manufacturer. To this end, the medium was aspirated and in eachcase 30 μl of LIVE/DEAD reagent per microtitre plate well were added tothe cells, which were then incubated for 30 minutes. The cells were thenwashed with PBS (phosphate-buffered saline). The number of live cellswas analysed by measuring the green fluorescence of the live dyecalcein-AM as a component of the LIVE/DEAD reagent using a fluorescenceplate reader (Flexstation, from Molecular Devices) at an excitationwavelength of 485 nM and an emission wavelength of 525 nM (Oral et al.1998). Cells only with cell culture medium, without added testcompounds, were treated in parallel and analysed as growth controls. Thereference compounds used for anti-tumour agents having a cytotoxic orproliferation-inhibiting action were colchicine (from Merck/Calbiochem,order No 234115) and Taxol (baccatin III N-benzyl-b-phenylisoserineester, from Merck/Calbiochem, order No. 580555) (Schiff and Horwitz1980; Holmes et al., 1991). The cytotoxic effects of the test compoundswere expressed as logarithmic GI₅₀ values ((growth)-inhibitinglogarithmic concentration value at which a cell growth reduced by 50%compared to the control without test compounds was measured; Xia et al.,2001; Smith et al., 2005).

TABLE 2 Inhibition of the cell proliferation in the presence of testcompounds according to the LIVE/DEAD cytotoxicity assay protocol ondifferent human tumour cell lines, log GI₅₀ values (M) Example No. A375cells SW620 cells HeLa cells colchicine 7.7 7.5 7.8 Taxol 6.7 6.9 7.8177 8.1 6.7 >8 117 6.6 6.6 6.8 345 6.3 6.4 6.6

Alternatively to the cell growth analysis in microtitre plates, thedifferent cells were also cultivated on slides and incubated analogouslywith the test compounds. As described, the cells were treated with thereagents from the LIVE/DEAD Assay Kit according to the instructions ofthe manufacturer and then studied using a fluorescence microscope.

1. A compound of formula (I)

in which the symbols are as defined below R¹ represents hydrogen, alkylhaving 1 to 10 carbon atoms which is unsubstituted or mono- topentasubstituted by identical or different substituents selected fromthe group consisting of halogen, cyano, hydroxyl, alkoxy having 1 to 4carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthiohaving 1 to 4 carbon atoms, amino, and mono- or dialkylamino having ineach case 1 to 4 carbon atoms, or R¹ represents alkenyl having 2 to 10carbon atoms which is unsubstituted or mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms,cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio having 1 to 4carbon atoms, amino, and mono- or dialkylamino having in each case 1 to4 carbon atoms, or R¹ represents alkynyl having 2 to 10 carbon atomswhich is unsubstituted or mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3to 6 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms,amino, and mono- or dialkylamino having in each case 1 to 4 carbonatoms, or R¹ represents cycloalkyl having 3 to 10 carbon atoms which isunsubstituted or mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms, or R¹ represents saturated or unsaturatedheterocyclyl having 3 to 10 ring members and 1 to 3 heteroatoms, such asnitrogen, oxygen or sulphur, where the heterocyclyl is unsubstituted ormono- or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms,cyano, nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxyl, alkoxyhaving 1 to 4 carbon atoms or mercapto; R² represents hydrogen or alkylhaving 1 to 6 carbon atoms; R¹ and R² together with the nitrogen atom towhich they are attached represent a saturated or unsaturatedheterocyclic ring having 3 to 8 ring members, where the heterocycleoptionally contains a further nitrogen, oxygen or sulphur atom as ringmember and where the heterocycle may be unsubstituted or mono- totrisubstituted by fluorine, chlorine, bromine, alkyl having 1 to 4carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorineor chlorine atoms, hydroxyl, alkoxy having 1 to 4 carbon atoms,haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine or chlorineatoms, mercapto, thioalkyl having 1 to 4 carbon atoms or haloalkylthiohaving 1 to 4 carbon atoms and 1 to 9 fluorine or chlorine atoms; R³represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₃-C₈-cycloalkyl, phenyl-C₁-C₁₀-alkyl, where R³ is unsubstituted orpartially or fully halogenated or optionally carries one to threeradicals from the group R^(x), or C₁-C₁₀-haloalkyl which optionallycarries one to three radicals from the group R^(x), and R^(x) representscyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy andoptionally halogenated oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy,oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy, oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy, or R³represents phenyl which may be mono- to tetrasubstituted by identical ordifferent substituents selected from the group consisting of halogen,cyano, nitro, amino, hydroxyl, formyl, carboxyl, carboxyalkyl,carbamoyl, and thiocarbamoyl; in each case straight-chain or branchedalkyl, alkoxy, alkylthio, alkyl-sulphinyl or alkylsulphonyl having ineach case 1 to 6 carbon atoms; in each case straight-chain or branchedalkenyl or alkenyloxy having in each case 2 to 6 carbon atoms; in eachcase straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio,haloalkylsulphinyl or haloalkylsulphonyl having in each case 1 to 6carbon atoms and 1 to 13 identical or different halogen atoms; in eachcase straight-chain or branched haloalkenyl or haloalkenyloxy having ineach case 2 to 6 carbon atoms and 1 to 11 identical or different halogenatoms; in each case straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties; cycloalkyl having 3 to 8 carbonatoms; 2,3-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy(—O—CH₂—O—) or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—), where these radicalsmay be mono- or polysubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms and haloalkyl having 1 to 4 carbon atoms and 1 to 9identical or different halogen atoms; or R³ represents saturated orfully or partially unsaturated or aromatic heterocyclyl having 3 to 8ring members and 1 to 3 heteroatoms selected from the group consistingof nitrogen, oxygen and sulphur, where the heterocyclyl may be mono- ordisubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,haloalkoxy having 1 to 4 carbon atoms, haloalkylthio having 1 to 4carbon atoms, hydroxyl, mercapto, cyano, nitro or cycloalkyl having 3 to6 carbon atoms or carboxyalkyl; R³ represents C₁-C₈-alkylamino,C₂-C₈alkenylamino, C₂-C₈alkynylamino, di-C₁-C₈-alkylamino,di-C₂-C₈-alkenylamino, di-C₂-C₈-alkynylamino,C₂-C₈-alkenyl-(C₂-C₈)-alkynylamino, C₂-C₆-alkynyl-(C₁-C₈)-alkylamino,C₂-C₈-alkenyl-(C₁-C₈)-alkylamino, C₆-C₁₀-arylamino,C₆-C₁₀-aryl-(C₁-C₈)-alkylamino,C₆-C₁₀-aryl-(C₁-C₄)-alkyl-(C₁-C₈)-alkylamino,heterocyclyl-(C₁-C₈)-alkylamino orheterocyclyl-(C₁-C₄)-alkyl-(C₁-C₈)-alkylamino; R⁴ represents CONR⁶R⁷; R⁵represents H, halogen, (C₁-C₄)-alkyl which is unsubstituted orsubstituted by one or more halogen atoms, cyclopropyl which isunsubstituted or substituted by one or more halogen atoms; SCH₃, SOCH₃,SO₂CH₃ or OCH₃; X represents H, fluorine, chlorine, bromine, CN,hydroxyl, alkoxy having 1 to 4 carbon atoms or alkylthio having 1 to 4carbon atoms; R⁶ represents H, an alkali metal or alkaline earth metal,copper, NH₄, mono-(C₁-C₁₀)-alkylammonium, di-(C₁-C₁₀)-alkylammonium,tri-(C₁-C₁₀)-alkylammonium, tetra-(C₁-C₁₀)-alkylammonium, where thealkyl radicals of the ammonium ions may be substituted by aryl orhydroxyl, cholinium, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, aryl, phenyl-C₁-C₁₀-alkyl, whereR⁶ is unsubstituted or partially or fully halogenated or optionallycarries one to three radicals from the group R^(x), or C₁-C₁₀-haloalkylwhich optionally carries one to three radicals from the group R^(x), andR^(x) represents cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl,C₃-C₆-alkynyloxy and optionally halogenatedoxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy, oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy,oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy or CONR⁶R⁷, CONR⁷OR⁷, COOR⁸,carboxy-(C₁-C₄)-alkyl; R⁷ represents COR^(S), S(O)₁₋₂R⁸, cyano, COOR⁸,CON(R⁸)₂, or

A, B, D, E, G are identical or different and are CR⁹, CR⁹R⁹, N, NR⁹, Oor S, with the proviso that at least one symbol represents N, O or S andthat the oxygen atoms are not adjacent to one another; Y represents C,CR⁹ or N; R⁸ represents H, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, aryl, phenyl-C₁-C₁₀-alkyl, whereR⁸ is unsubstituted or partially or fully halogenated or optionallycarries one to three radicals selected from the group consisting ofR^(x), or C₁-C₁₀-haloalkyl which optionally carries one to threeradicals from the group R^(x), and R^(x) represents cyano, nitro,hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy andoptionally halogenated oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy,oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy, oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy; or tworadicals R⁸ form a cycle having 3 to 6 carbon atoms which is saturatedor partially unsaturated and optionally contains 1 or 2 further N, S orO atoms, where the oxygen atoms are not adjacent to one another; or R⁶and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they areattached form a 4- to 8-membered cycle which may contain one or moreheteroatoms selected from the group consisting of sulphur, oxygen andnitrogen, where oxygen atoms are not adjacent to one another; R⁹represents R⁷, halogen, NR⁷ ₂, OH, SR⁷ or OR⁷, or an agrochemicallyactive salt thereof.
 2. A compound of formula (I) according to claim 1,in which the symbols are as defined below R¹ represents hydrogen, alkylhaving 1 to 10 carbon atoms which is unsubstituted or mono- topentasubstituted by identical or different substituents selected fromthe group consisting of halogen, cyano, hydroxyl, alkoxy having 1 to 4carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthiohaving 1 to 4 carbon atoms, amino, and mono- or dialkylamino having ineach case 1 to 4 carbon atoms, or R¹ represents alkenyl having 2 to 10carbon atoms which is unsubstituted or mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms,cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio having 1 to 4carbon atoms, amino, and mono- or dialkylamino having in each case 1 to4 carbon atoms, or R¹ represents alkynyl having 2 to 10 carbon atomswhich is unsubstituted or mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3to 6 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms,amino, and mono- or dialkylamino having in each case 1 to 4 carbonatoms, or R¹ represents cycloalkyl having 3 to 10 carbon atoms which isunsubstituted or mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen and alkylhaving 1 to 4 carbon atoms, or R¹ represents saturated or unsaturatedheterocyclyl having 3 to 10 ring members and 1 to 3 heteroatoms, such asnitrogen, oxygen or sulphur, where the heterocyclyl is unsubstituted ormono- or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms,cyano, nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxyl, alkoxyhaving 1 to 4 carbon atoms or mercapto; R² represents hydrogen or alkylhaving 1 to 6 carbon atoms; R¹ and R² together with the nitrogen atom towhich they are attached represent a saturated or unsaturatedheterocyclic ring having 3 to 8 ring members, where the heterocycleoptionally contains a further nitrogen, oxygen or sulphur atom as ringmember and where the heterocycle may be unsubstituted or mono- totrisubstituted by fluorine, chlorine, bromine, alkyl having 1 to 4carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorineor chlorine atoms, hydroxyl, alkoxy having 1 to 4 carbon atoms,haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine or chlorineatoms, mercapto, thioalkyl having 1 to 4 carbon atoms or haloalkylthiohaving 1 to 4 carbon atoms and 1 to 9 fluorine or chlorine atoms; R³represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₃-C₈-cycloalkyl, phenyl-C₁-C₁₀-alkyl, where R³ is unsubstituted orpartially or fully halogenated or optionally carries one to threeradicals from the group R^(x), or C₁-C₁₀-haloalkyl which optionallycarries one to three radicals from the group R^(x), and R^(x) representscyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy andoptionally halogenated oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy,oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy, oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy, or R³represents phenyl which may be mono- to tetrasubstituted by identical ordifferent substituents selected from the group consisting of halogen,cyano, nitro, amino, hydroxyl, formyl, carboxyl, carboxyalkyl,carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl,alkoxy, alkylthio, alkyl-sulphinyl or alkylsulphonyl having in each case1 to 6 carbon atoms; in each case straight-chain or branched alkenyl oralkenyloxy having in each case 2 to 6 carbon atoms; in each casestraight-chain or branched haloalkyl, haloalkoxy, haloalkylthio,haloalkylsulphinyl or haloalkylsulphonyl having in each case 1 to 6carbon atoms and 1 to 13 identical or different halogen atoms; in eachcase straight-chain or branched haloalkenyl or haloalkenyloxy having ineach case 2 to 6 carbon atoms and 1 to 11 identical or different halogenatoms; in each case straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties; cycloalkyl having 3 to 8 carbonatoms; and 2,3-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy(—O—CH₂—O—) or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—), where these radicalsare optionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen, alkyl having1 to 4 carbon atoms and haloalkyl having 1 to 4 carbon atoms and 1 to 9identical or different halogen atoms; or R³ represents saturated orfully or partially unsaturated or aromatic heterocyclyl having 3 to 8ring members and 1 to 3 heteroatoms selected from the group consistingof nitrogen, oxygen and sulphur, where the heterocyclyl may be mono- ordisubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,haloalkoxy having 1 to 4 carbon atoms, haloalkylthio having 1 to 4carbon atoms, hydroxyl, mercapto, cyano, nitro or cycloalkyl having 3 to6 carbon atoms or carboxyalkyl; R³ represents C₁-C₈-alkylamino,C₂-C₈alkenylamino, C₂-C₈-alkynylamino, di-C₁-C₈-alkylamino,di-C₂-C₈-alkenylamino, di-C₂-C₈-alkynylamino,C₂-C₈-alkenyl-(C₂-C₈)-alkynylamino, C₂-C₆-alkynyl-(C₁-C₈)-alkylamino,C₂-C₈-alkenyl-(C₁-C₈)-alkylamino, C₆-C₁₀-arylamino,C₆-C₁₀-aryl-(C₁-C₈)-alkylamino,C₆-C₁₀-aryl-(C₁-C₄)-alkyl-(C₁-C₈)-alkylamino,heterocyclyl-(C₁-C₈)-alkylamino orheterocyclyl-(C₁-C₄)-alkyl-(C₁-C₈)-alkylamino; R⁴ represents CONR⁶R⁷; R⁵represents H, halogen, (C₁-C₄)-alkyl which is unsubstituted orsubstituted by one or more halogen atoms, cyclopropyl which isunsubstituted or substituted by one or more halogen atoms; SCH₃, SOCH₃,SO₂CH₃ or OCH₃; X represents H, fluorine, chlorine, bromine, CN,hydroxyl, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4carbon atoms or (C₁-C₇)-alkyl or (C₁-C₃)-haloalkyl; R⁶ represents H, analkali metal or alkaline earth metal, copper, NH₄,mono-(C₁-C₁₀)-alkylammonium, di-(C₁-C₁₀)-alkylammonium,tri-(C₁-C₁₀)-alkylammonium, tetra-(C₁-C₁₀)-alkylammonium, where thealkyl radicals of the ammonium ions may be substituted by aryl orhydroxyl, cholinium, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, aryl, phenyl-C₁-C₁₀-alkyl, whereR⁶ is unsubstituted or partially or fully halogenated or optionallycarries one to three radicals from the group R^(x), or C₁-C₁₀-haloalkylwhich optionally carries one to three radicals from the group R^(x), andR^(x) represents cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl,C₃-C₆-alkynyloxy and optionally halogenatedoxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy, oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy,oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy or CONR⁶R⁷, CONR⁷OR⁷, COOR⁸,carboxy-(C₁-C₄)-alkyl; R⁷ represents COR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸,CON(R⁸)₂, where the radicals R⁸ may be identical or different, or

A, B, D, E, G are identical or different and are CR⁹, CR⁹R⁹, N, NR⁹, Oor S, with the proviso that at least one symbol represents N, O or S andthat the oxygen atoms are not adjacent to one another; Y represents C,CR⁹ or N; R⁸ independently of the other radicals represents H,C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkenyl, aryl, phenyl-C₁-C₁₀-alkyl, where R⁸ is unsubstitutedor partially or fully halogenated or optionally carries one to threeradicals from the group R^(x), or C₁-C₁₀-haloalkyl which optionallycarries one to three radicals selected from the group consisting ofR^(x), and R^(x) represents cyano, nitro, hydroxyl, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl, C₃-C₆-alkynyloxy andoptionally halogenated oxy-C₁-C₄-alkyl-C₁-C₄-alkenoxy,oxy-C₁-C₄-alkenyl-C₁-C₄-alkoxy, oxy-C₁-C₄-alkyl-C₁-C₄-alkyloxy; or tworadicals R⁸ form a cycle having 3 to 6 carbon atoms which is saturatedor partially unsaturated and optionally contains 1 or 2 further N, S orO atoms, where the oxygen atoms are not adjacent to one another; or R⁶and R⁸ together with the N—CO or N—S(O)₁₋₂ group to which they areattached form a 4- to 8-membered cycle which may contain one or moreheteroatoms selected from the group consisting of sulphur, oxygen andnitrogen, where oxygen atoms are not adjacent to one another; R⁹represents R⁷, H, halogen, NR⁷ ₂, OH, SR⁷ or OR⁷.
 3. A compound offormula (I) according to claim 1 in which the symbols are as definedbelow R¹ represents hydrogen or a radical of the formula

where # denotes the point of attachment and the radicals may be presentin optically pure form or as isomer mixtures; R² represents hydrogen,methyl, ethyl, propyl, or R¹ and R² together with the nitrogen atom towhich they are attached represent pyrrolidinyl, piperidinyl,morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-1(2H)-pyridinylor tetrahydro-1(2H)-pyridazinyl, where these radicals are unsubstitutedor substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups ortrifluoromethyl, or R¹ and R² together with the nitrogen atom to whichthey are attached represent a radical of the formula

in which R′ represents hydrogen or methyl, R″ represents methyl, ethyl,fluorine, chlorine or trifluoromethyl, m represents the number 0, 1, 2or 3, where R″ represents identical or different radicals if mrepresents 2 or 3, R′″ represents methyl, ethyl, fluorine, chlorine ortrifluoromethyl and n represents the number 0, 1, 2 or 3, where R′″represents identical or different radicals if n represents 2 or 3, R³represents (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, where R³ is unsubstitutedor substituted by one or more fluorine or chlorine atoms, benzyl or R³represents phenyl which may be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl,n-, s- or t-butyl, vinyl, ethynyl, allyl, propargyl, methoxy, ethoxy, n-or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl,trichloroethynyloxy, trifluoroethynyloxy, chloro-allyloxy,iodopropargyloxy, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxy-carbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl,methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl,cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, or by 2,3-attached1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—) or1,2-ethylenedioxy (—O—CH₂—CH₂—O—), where these radicals may be mono- orpolysubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, methyl, ethyl, n-propyl,i-propyl, trifluoromethyl, carboxyl and carboxymethyl, R³ representspyridyl which is attached in the 2- or 4-position and may be mono- totetrasubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, bromine, cyano, hydroxyl, mercapto,nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl,hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl,carboxyl and carboxymethyl or R³ represents pyrimidyl which is attachedin the 2- or 4-position and may be mono- to trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl,ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl,methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxyl andcarboxymethyl or R³ represents thienyl which is attached in the 2- or3-position and may be mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or R³represents C₁-C₈-alkylamino or di-C₁-C₈-alkylamino, or R³ representsthiazolyl which is attached in the 2-, 4- or 5-position and may be mono-or disubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, cyano, nitro,hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or R³represents N-piperidinyl, N-tetrazolyl, N-pyrazolyl, N-imidazolyl,N-1,2,4-triazolyl, N-pyrrolyl or N-morpholinyl which are in each caseunsubstituted or mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl and trifluoromethyl, R⁴ represents CONR⁶R⁷; R⁵represents H, Cl, F, CH₃, —CH(CH₃)₂ or cyclopropyl; X represents H, F,Cl, CN, C₁-C₄-alkyl which is unsubstituted or substituted by one or morefluorine or chlorine atoms; R⁶ represents H, Na, K, ½Ca, ½Mg, Cu, NH₄,NH(CH₃)₃, N(CH₃)₄, HN(C₂H₅)₃, N(C₂H₅)₄, H₂N(iC₃H₇)₂, H₃NCH₂Ph,(H₃C)₃NCH₂Ph, cholinium, (C₁-C₈)-alkyl, (C₃-C₆)-alkenyl,(C₃-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl, phenyl, benzyl; R⁷ representsCOR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂, pyrrolyl, imidazolyl,pyrazolyl, 1,3,4-triazolyl, thiazolyl, isothiazolyl, 1,3,4-oxadiazolyl,1,3,4-thiadiazolyl, oxazolyl, isoxazolyl, tetrazolyl, oxadiazinyl,4H-[1,2,4]-oxadiazin-3-yl, dioxazinyl,5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, pyrimidinyl, pyrazinyl,pyridazinyl, where the heterocyclic radicals are optionally substitutedby one or more radicals selected from the group consisting ofC₁-C₄-alkyl, C₁-C₄-alkoxy and halogen; R⁸ represents H, (C₁-C₈)-alkyl,(C₃-C₆)-alkenyl, propargyl, (C₃-C₈)-cycloalkyl, benzyl; or two radicalsR⁸ form a cycle having 3 to 6 carbon atoms which is saturated orpartially unsaturated and optionally contains 1 or 2 further N, S or Oatoms, where the oxygen atoms are not adjacent; or R⁶ and R⁸ togetherwith the N—CO or N—S(O)₁₋₂ group to which they are attached form a 4- to8-membered cycle which may contain one or more heteroatoms selected fromthe group consisting of sulphur, oxygen and nitrogen, where oxygen atomsare not adjacent.
 4. A compound of formula (I) according to claim 1 inwhich the symbols are as defined below R¹ represents hydrogen or aradical of the formula

where # denotes the point of attachment where the radicals may bepresent in optically pure form or as isomer mixtures; R² representshydrogen, methyl, ethyl, propyl, or R¹ and R² together with the nitrogenatom to which they are attached represent pyrrolidinyl, piperidinyl,morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-1(2H)-pyridinylor tetrahydro-1(2H)-pyridazinyl, where these radicals are unsubstitutedor substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups ortrifluoromethyl, or R¹ and R² together with the nitrogen atom to whichthey are attached represent a radical of the formula

in which R′ represents hydrogen or methyl, R″ represents methyl, ethyl,fluorine, chlorine or trifluoromethyl, m represents the number 0, 1, 2or 3, where R″ represents identical or different radicals if mrepresents 2 or 3, R′″ represents methyl, ethyl, fluorine, chlorine ortrifluoromethyl and n represents the number 0, 1, 2 or 3, where R′″represents identical or different radicals if n represents 2 or 3, R³represents (C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl,(C₃-C₈)-cycloalkyl or benzyl, where R³ is unsubstituted or substitutedby one or more fluorine or chlorine atoms or alkyl, or R³ representsphenyl which may be mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, vinyl, ethynyl, allyl, propargyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl, allyloxy, propargyloxy,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, trichloroethynyloxy, trifluoroethynyloxy,chloro-allyloxy, iodopropargyloxy, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxy-carbonyl, ethoxycarbonyl, hydroximinomethyl,hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl,ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, orby 2,3-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy(—O—CH₂—O—) or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—), where these radicalsmay be mono- or polysubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, methyl, ethyl,n-propyl, i-propyl, trifluoromethyl, carboxyl and carboxymethyl, R³represents pyridyl which is attached in the 2- or 4-position and may bemono- to tetrasubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,cyano, hydroxyl, mercapto, nitro, methyl, ethyl, methoxy, methylthio,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or R³represents pyrimidyl which is attached in the 2- or 4-position and maybe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or R³represents thienyl which is attached in the 2- or 3-position and may bemono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, cyano, nitro,hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or R³represents C₁-C₈-alkylamino or di-C₁-C₈-alkylamino, or R³ representsthiazolyl which is attached in the 2-, 4- or 5-position and may be mono-or disubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, cyano, nitro,hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, carboxyl and carboxymethyl or R³represents N-piperidinyl, N-tetrazolyl, N-pyrazolyl, N-imidazolyl,N-1,2,4-triazolyl, N-pyrrolyl or N-morpholinyl which are in each caseunsubstituted or mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl and trifluoromethyl, R⁴ represents CONR⁶R⁷; R⁵represents H, Cl, F, CH₃, —CH(CH₃)₂ or cyclopropyl; X represents H, F,Cl, CN, C₁-C₄-alkyl which is unsubstituted or substituted by one or morefluorine or chlorine atoms; R⁶ represents H, Na, K, ½Ca, ½Mg, Cu, NH₄,NH(CH₃)₃, N(CH₃)₄, HN(C₂H₅)₃, N(C₂H₅)₄, H₂N(iC₃H₇)₂, H₃NCH₂Ph,(H₃C)₃NCH₂Ph, cholinium, (C₁-C₈)-alkyl, (C₃-C₆)-alkenyl,(C₃-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl, phenyl, benzyl; R⁷ representsCOR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂, pyrrolyl, imidazolyl,pyrazolyl, 1,3,4-triazolyl, thiazolyl, isothiazolyl, 1,3,4-oxadiazolyl,1,3,4-thiadiazolyl, oxazolyl, isoxazolyl, tetrazolyl, oxadiazinyl,4H-[1,2,4]-oxadiazin-3-yl, dioxazinyl,5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, pyrimidinyl, pyrazinyl,pyridazinyl, where the heterocyclic radicals are optionally substitutedby one or more radicals selected from the group consisting ofC₁-C₄-alkyl, C₁-C₄-alkoxy and halogen; R⁸ represents H, (C₁-C₈)-alkyl,(C₁-C₈)-haloalkyl, (C₃-C₆)-alkenyl, propargyl, (C₃-C₈)-cycloalkyl,benzyl; or two radicals R⁸ form a cycle having 3 to 6 carbon atoms whichis saturated or partially unsaturated and optionally contains 1 or 2further N, S or O atoms, where oxygen atoms are not adjacent to oneanother; Or R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to whichthey are attached form a 4- to 8-membered cycle which may contain one ormore heteroatoms selected from the group consisting of sulphur, oxygenand nitrogen, where oxygen atoms are not adjacent to one another.
 5. Acompound of formula (I) according to claim 1, where the symbols are asdefined below R³ represents (C₁-C₆)-alkyl, (C₃-C₆)-alkenyl,(C₃-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, where R³ is unsubstituted orsubstituted by one or more fluorine or chlorine atoms or alkyl, or R³represents 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substitutedphenyl or represents 2,4,6- or 2,4,5-trisubstituted phenyl havingsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, carboxyl and carboxymethyl or R³ represents pyridylwhich is attached in the 2- or 4-position and may be mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, cyano, hydroxyl,mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl,hydroximino ethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl,and carboxymethyl or R³ represents pyrimidyl which is attached in the4-position and may be mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio,hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, trifluoromethyl, and carboxymethyl or R³ representsthienyl which is attached in the 2- or 3-position and may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxyl,mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl,hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl,carboxyl and carboxymethyl or R⁴ represents CONR⁶R⁷; R⁵ represents H,—CH₃, —CH(CH₃)₂, Cl or cyclopropyl; and X represents fluorine, chlorine,(C₁-C₇)-alkyl or (C₁-C₃)-haloalkyl; R⁶ represents H, Na, K, NH₄,HN(Et)₂, H₂N(iPr)₂, H₃NCH₂Ph, (H₃C)₃NCH₂Ph, benzyl, (C₃-C₈)-cycloalkyl,propargyl, (C₃-C₆)-alkenyl, (C₁-C₈)-alkyl, fully or partiallysubstituted by F or Cl or carboxy-(C₁-C₄)-alkyl, CONR⁶R⁷, CONR⁷OR⁷,COOR⁸; R⁷ represents COR⁸, S(O)₁₋₂R⁸, cyano, COOR⁸, CON(R⁸)₂,1H-pyrrolyl, 1H-imidazolyl, 1H-pyrazolyl, isoxazolyl, oxazolyl,1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl,1H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H-[1,2,4]-oxadiazin-3-yl,dioxazinyl, 5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, where theheterocyclic radicals are optionally substituted by one or more radicalsfrom the group consisting of C₁-C₄-alkyl and halogen; R⁸ represents H,(C₁-C₈)-alkyl, (C₃-C₆)-alkenyl, propargyl, (C₃-C₈)-cycloalkyl, benzyl;or two radicals R⁸ form a cycle having 3 to 6 carbon atoms which issaturated or partially unsaturated and optionally contains 1 or 2further N, S or O atoms, where oxygen atoms are not adjacent to oneanother; or R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to whichthey are attached form a 4- to 8-membered cycle which may contain one ormore heteroatoms selected from the group consisting of sulphur, oxygenand nitrogen, where oxygen atoms are not adjacent to one another.
 6. Acompound of formula (I) according to claim 1 in which the symbols are asdefined below R¹ represents hydrogen or a radical of the formula

where # denotes the point of attachment where the radicals may bepresent in optically pure form or as isomer mixtures; R² representshydrogen, methyl, ethyl, propyl, or R¹ and R² together with the nitrogenatom to which they are attached represent pyrrolidinyl, piperidinyl,morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-1(2H)-pyridinylor tetrahydro-1(2H)-pyridazinyl, where these radicals are unsubstitutedor substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups ortrifluoromethyl, or R¹ and R² together with the nitrogen atom to whichthey are attached represent a radical of the formula

in which R′ represents hydrogen or methyl, R″ represents methyl, ethyl,fluorine, chlorine or trifluoromethyl, m represents the number 0, 1, 2or 3, where R″ represents identical or different radicals if mrepresents 2 or 3, R′″ represents methyl, ethyl, fluorine, chlorine ortrifluoromethyl and n represents the number 0, 1, 2 or 3, where R′″represents identical or different radicals if n represents 2 or 3, R³represents 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substitutedphenyl or represents 2,4,6- or 2,4,5-trisubstituted phenyl havingsubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy,methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl,methoximinoethyl, carboxyl and carboxymethyl or R³ represents thienylwhich is attached in the 2- or 3-position and may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxyl,mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl,hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl,carboxyl and carboxymethyl or R⁴ represents CONR⁶R⁷; R⁵ represents H,—CH₃; X represents fluorine, chlorine, methyl or trifluoromethyl; R⁶represents H, Na, K, NH₄, HN(Et)₂, H₂N(iPr)₂, H₃NCH₂Ph, (H₃C)₃NCH₂Ph,benzyl, (C₃-C₈)-cycloalkyl, propargyl, (C₃-C₆)-alkenyl, (C₁-C₈)-alkyl,fully or partially substituted by F or Cl or carboxy-(C₁-C₄)-alkyl,CONR⁶R⁷, CONR⁷OR⁷, COOR⁸; R⁷ represents COR⁸, S(O)R⁸, COOR⁸,1H-pyrrolyl, 1H-imidazolyl, 1H-pyrazolyl, isoxazolyl, oxazolyl,1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl,1H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H-[1,2,4]-oxadiazin-3-yl,dioxazinyl, 5,6-dihydro-[1,4,2]-dioxazin-3-yl, pyridyl, where theheterocyclic radicals are optionally substituted by one or more radicalsselected from the group consisting of C₁-C₄-alkyl and halogen; R⁸independently of the other radicals represents H, methyl, ethyl, propyl,i-propyl, butyl, i-butyl, sec-butyl, t-butyl, pentyl, hexyl,(C₁-C₃)-haloalkyl, (C₂-C₆)-alkenyl, propargyl, (C₃-C₆)-cycloalkyl,benzyl; or R⁶ and R⁸ together with the N—CO or N—S(O)₁₋₂ group to whichthey are attached form a 4- to 8-membered cycle which may contain one ormore heteroatoms selected from the group consisting of sulphur, oxygenand nitrogen, where oxygen atoms are not adjacent to one another.
 7. Acomposition for controlling unwanted microorganisms, comprising at leastone compound of the formula (I) according to claim 1, and an extender ora surfactant or a combination thereof.
 8. A composition according toclaim 7, further comprising at least one additional compound selectedfrom the group consisting of fungicides, bactericides, acaricides,nematicides, and insecticides.
 9. A process for preparing a compound ofthe formula (I) according to claim 1 in which X represents chlorine andR⁴ represents CONR⁶R⁷, comprising a) reacting a substituted3-aminopyrazole derivative of the formula II,

with a malonic ester of the formula IIa

where R¹⁰ represents C₁-C₄-alkyl and R¹¹ represents C₁-C₈-alkyl or arylto give a dihydroxypyrazolopyrimidine III

b) halogenation of a compound of formula III to give ahalopyrazolopyrimidine IV

c) reaction of a compound of formula IV with an amine to give a7-aminopyrazolopyrimidine V

d) hydrolysis of a compound of formula (V) to give apyrazolopyrimidinecarboxylic acid VI

e) reaction of a compound of formula (VI) with a chlorinating agent togive a pyrazolopyrimidine acid chloride VII

and f) reaction of a compound of formula VII with HNR⁶R⁷ to give acompound of the formula (Ia)